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Name
BORRELIDIN
- EINECS
- CAS No. 7184-60-3
- Article Data5
- CAS DataBase
- Density 1.14 g/cm3
- Solubility DMSO: 1 mg/mL
- Melting Point 143-145℃
- Formula C28H43NO6
- Boiling Point 710.3 °C at 760 mmHg
- Molecular Weight 489.653
- Flash Point 383.4 °C
- Transport Information
- Appearance White to off-white powder
- Safety
- Risk Codes
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Molecular Structure
- Hazard Symbols
- Synonyms 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecar boxylic acid;Treponemycin;NSC 216128;BRN 0066270;AC1O5MFI;B1936_SIGMA;(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid;
- PSA 127.85000
- LogP 4.63558
Synthetic route
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631919-63-6
(1'R,1S,2S,2'R,8R,9S,11R,13S,15S,16S)-2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentane-1'-carboxylic acid 2-trimethylsilanyl-ethyl ester
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h; | 94% |
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With dimethylboron bromide In dichloromethane at -78℃; for 1h; |
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768395-41-1
(1R,2R)-2-((4E,6Z)-(2S,9S,11R,13S,15S,16S)-7-Cyano-16-hydroxy-9,11,13,15-tetramethyl-8,18-dioxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid
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A
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; cerium(III) chloride In methanol at 0℃; for 1h; Luche reaction; Title compound not separated from byproducts; |
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 48h; | 5.2 mg |
| With pyridine; pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 48h; | 5.20 mg |
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 28 steps 1.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11.1: Et3N / benzene / 1 h / 20 °C 12.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 13.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 15.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 15.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: DMAP / pentane / 168 h / 20 °C 16.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 17.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 18.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 19.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 20.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 21.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 24.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 25.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 28.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 27 steps 1.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11.1: Et3N / benzene / 1 h / 20 °C 12.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 13.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 15.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 15.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: DMAP / pentane / 168 h / 20 °C 16.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 17.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 18.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 19.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 20.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 23.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 24.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 25.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 26.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 27.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 20 steps 1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11: Et3N / benzene / 1 h / 20 °C 12: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 13: 93 percent / PPTS / ethanol / 10 h / 50 °C 14: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 15: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 16: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 17: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 18: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 20: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 22 steps 1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 2: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 6: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 7: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 11: Et3N / benzene / 1 h / 20 °C 12: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 13: 93 percent / PPTS / ethanol / 10 h / 50 °C 14: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 15: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 16: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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714973-96-3
(2S,4R,8S,Z)-9-(tert-butyldiphenylsilyloxy)-2,4,6,8-tetramethylnon-3-en-1-ol
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 25 steps 1.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8.1: Et3N / benzene / 1 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 24 steps 1.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8.1: Et3N / benzene / 1 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 17 steps 1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8: Et3N / benzene / 1 h / 20 °C 9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 10: 93 percent / PPTS / ethanol / 10 h / 50 °C 11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 13: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 19 steps 1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 2: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 3: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 4: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 6: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 8: Et3N / benzene / 1 h / 20 °C 9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 10: 93 percent / PPTS / ethanol / 10 h / 50 °C 11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 13: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 15: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 16: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 17: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 19: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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935872-55-2
C42H66O6SiNCOCF3
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 4: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 8: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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935872-03-0
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 14 steps 1.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 1.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: DMAP / pentane / 168 h / 20 °C 2.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 3.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 5.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 6.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 7.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 10.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 13 steps 1.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 1.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: DMAP / pentane / 168 h / 20 °C 2.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 3.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 5.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 6.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 9.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 10.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 13.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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935872-04-1
(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 18 steps 1.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 2.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 3.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 5.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 5.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6.1: DMAP / pentane / 168 h / 20 °C 6.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 8.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 9.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 10.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 11.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 14.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 15.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 18.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 17 steps 1.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 2.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 3.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 5.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 5.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6.1: DMAP / pentane / 168 h / 20 °C 6.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 8.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 9.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 10.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 13.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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-
935872-05-2
(S,2Z,4E)-allyl 2-bromo-7-hydroxy-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate
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-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 17 steps 1.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 2.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 4.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 4.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5.1: DMAP / pentane / 168 h / 20 °C 5.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 8.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 9.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 10.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 13.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 16 steps 1.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 2.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 4.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 4.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5.1: DMAP / pentane / 168 h / 20 °C 5.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 7.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 8.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 9.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 12.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 13.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 16.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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935872-06-3
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-(allyloxy)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-(tetrahydro-2H-pyran-2-yloxy)undecanoate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 16 steps 1.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 2.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 3.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 3.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4.1: DMAP / pentane / 168 h / 20 °C 4.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 5.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 6.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 7.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 8.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 9.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 12.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 13.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 16.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 15 steps 1.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 2.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 3.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 3.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4.1: DMAP / pentane / 168 h / 20 °C 4.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 5.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 6.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 7.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 8.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 11.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 12.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 13.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 15.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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-
935872-07-4
(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-(allyloxy)-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 15 steps 1.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 2.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 2.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: DMAP / pentane / 168 h / 20 °C 3.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 4.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 5.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 6.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 7.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 8.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 9.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 11.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 12.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 13.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 15.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 14 steps 1.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 2.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 2.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: DMAP / pentane / 168 h / 20 °C 3.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 4.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 5.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 6.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 7.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 8.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 10.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 13 steps 1.1: DMAP / pentane / 168 h / 20 °C 1.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 2.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 4.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 5.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 6.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 9.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 10.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 13.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 12 steps 1.1: DMAP / pentane / 168 h / 20 °C 1.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 2.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 4.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 5.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 6.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 8.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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935872-09-6
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 16-(tert-butyldimethylsilyloxy)-8-hydroxy-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 12 steps 1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 3: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 4: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 5: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 8: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 11 steps 1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 3: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 4: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 5: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 7: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 11: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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935872-10-9
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-allyl 8,16-bis(tert-butyldimethylsilyloxy)-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylate
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-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 11 steps 1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 2: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 3: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 4: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 5: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 6: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 7: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 8: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 9: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 11: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 10 steps 1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 2: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 3: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 4: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 6: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 8: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 10: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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-
935872-12-1
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-16-(tert-butyldimethylsilyloxy)-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxylic acid
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 10 steps 1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 2: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 3: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 4: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 5: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 6: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 7: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 8: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 10: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 9 steps 1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 2: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 3: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 5: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 7: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 9: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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935872-13-2
(2S,4E,6E,8S,9S,11R,13S,15S,16S)-16-(tert-butyldimethylsilyloxy)-2-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-diene-7-carboxamide
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 9 steps 1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 2: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 3: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 4: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 5: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 6: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 7: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 9: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 8 steps 1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 4: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 7: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 8: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
57287-24-8
((1R,2R)-cyclopentane-1,2-diyl)dimethanol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 26 steps 1.1: NaH / dimethylformamide / -20 - 20 °C 2.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7.1: 73 percent / benzene / 48 h / 80 °C 8.1: 84 percent / benzene / 39 h / 70 °C 9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: DMAP / pentane / 168 h / 20 °C 14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 19.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 22.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 23.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 25 steps 1.1: NaH / dimethylformamide / -20 - 20 °C 2.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7.1: 73 percent / benzene / 48 h / 80 °C 8.1: 84 percent / benzene / 39 h / 70 °C 9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: DMAP / pentane / 168 h / 20 °C 14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 18.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 18 steps 1: NaH / dimethylformamide / -20 - 20 °C 2: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 3: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 4: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 5: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 6: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 7: 73 percent / benzene / 48 h / 80 °C 8: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 9: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 10: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 11: 93 percent / PPTS / ethanol / 10 h / 50 °C 12: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 14: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 15: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 16: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 18: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
90270-02-3, 97937-36-5
(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 34 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 21.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 21.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: DMAP / pentane / 168 h / 20 °C 22.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 23.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 24.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 25.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 26.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 27.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 28.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 29.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 30.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 31.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 32.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 33.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 34.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 33 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 21.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 21.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: DMAP / pentane / 168 h / 20 °C 22.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 23.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 24.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 25.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 26.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 29.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 30.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 31.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 32.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 33.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 26 steps 1.1: 98 percent / imidazole / CH2Cl2 / 0.5 h / 20 °C 2.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 3.1: imidazole / dimethylformamide / 0 - 20 °C 4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 6.2: tetrahydrofuran; hexane / 1 h / -30 °C 6.3: tetrahydrofuran; hexane / -20 °C 7.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 8.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 9.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 10.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 11.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 14.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 15.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 16.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 17.1: Et3N / benzene / 1 h / 20 °C 18.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 19.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 20.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 21.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 22.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 23.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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-
147782-80-7
(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 32 steps 1.1: imidazole / dimethylformamide / 0 - 20 °C 2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 4.2: tetrahydrofuran; hexane / 1 h / -30 °C 4.3: tetrahydrofuran; hexane / -20 °C 5.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 7.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 8.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 9.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 13.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 15.1: Et3N / benzene / 1 h / 20 °C 16.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 17.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 18.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 19.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 19.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: DMAP / pentane / 168 h / 20 °C 20.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 21.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 22.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 23.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 24.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 25.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 28.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 29.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 30.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 31.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 32.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 31 steps 1.1: imidazole / dimethylformamide / 0 - 20 °C 2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 4.2: tetrahydrofuran; hexane / 1 h / -30 °C 4.3: tetrahydrofuran; hexane / -20 °C 5.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 7.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 8.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 9.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 13.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 15.1: Et3N / benzene / 1 h / 20 °C 16.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 17.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 18.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 19.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 19.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: DMAP / pentane / 168 h / 20 °C 20.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 21.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 22.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 23.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 24.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 25.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 26.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 27.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 28.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 29.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 30.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 31.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 24 steps 1.1: imidazole / dimethylformamide / 0 - 20 °C 2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 4.2: tetrahydrofuran; hexane / 1 h / -30 °C 4.3: tetrahydrofuran; hexane / -20 °C 5.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 6.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 7.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 8.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 9.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 13.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 15.1: Et3N / benzene / 1 h / 20 °C 16.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 17.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 18.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 19.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
157837-64-4
(2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentan-1-ol
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 30 steps 1.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 2.2: tetrahydrofuran; hexane / 1 h / -30 °C 2.3: tetrahydrofuran; hexane / -20 °C 3.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 5.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 6.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 7.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 8.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 9.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 11.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 13.1: Et3N / benzene / 1 h / 20 °C 14.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 15.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 16.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 17.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 17.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: DMAP / pentane / 168 h / 20 °C 18.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 19.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 20.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 21.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 22.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 23.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 24.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 25.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 26.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 27.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 28.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 29.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 30.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 29 steps 1.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 2.2: tetrahydrofuran; hexane / 1 h / -30 °C 2.3: tetrahydrofuran; hexane / -20 °C 3.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 5.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 6.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 7.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 8.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 9.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 11.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 13.1: Et3N / benzene / 1 h / 20 °C 14.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 15.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 16.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 17.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 17.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: DMAP / pentane / 168 h / 20 °C 18.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 19.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 20.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 21.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 22.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 25.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 26.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 29.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 22 steps 1.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 2.2: tetrahydrofuran; hexane / 1 h / -30 °C 2.3: tetrahydrofuran; hexane / -20 °C 3.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 4.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 5.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 6.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 7.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 8.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 9.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 11.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 13.1: Et3N / benzene / 1 h / 20 °C 14.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 15.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 16.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 17.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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157837-65-5
(2R,4S)-5-{[tert-butyl(diphenyl)silyl]oxy}-2,4-dimethylpentanal
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 29 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 1.2: tetrahydrofuran; hexane / 1 h / -30 °C 1.3: tetrahydrofuran; hexane / -20 °C 2.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 3.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 4.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 5.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 6.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 10.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 12.1: Et3N / benzene / 1 h / 20 °C 13.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 14.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 15.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 16.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 16.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: DMAP / pentane / 168 h / 20 °C 17.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 18.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 19.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 20.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 21.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 22.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 25.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 26.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 29.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 28 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 1.2: tetrahydrofuran; hexane / 1 h / -30 °C 1.3: tetrahydrofuran; hexane / -20 °C 2.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 3.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 4.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 5.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 6.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 10.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 12.1: Et3N / benzene / 1 h / 20 °C 13.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 14.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 15.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 16.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 16.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: DMAP / pentane / 168 h / 20 °C 17.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 18.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 19.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 20.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 21.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 24.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 25.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 28.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 21 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 1.2: tetrahydrofuran; hexane / 1 h / -30 °C 1.3: tetrahydrofuran; hexane / -20 °C 2.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 3.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 4.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 5.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 6.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 7.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 8.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 10.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 12.1: Et3N / benzene / 1 h / 20 °C 13.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 14.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 15.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 16.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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335060-49-6
(2S,4R)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2,4-dimethylpentyl acetate
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 33 steps 1.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 2.1: imidazole / dimethylformamide / 0 - 20 °C 3.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 4.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 5.2: tetrahydrofuran; hexane / 1 h / -30 °C 5.3: tetrahydrofuran; hexane / -20 °C 6.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 7.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 8.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 9.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 10.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 11.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 14.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 16.1: Et3N / benzene / 1 h / 20 °C 17.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 18.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 19.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 20.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 20.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: DMAP / pentane / 168 h / 20 °C 21.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 22.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 23.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 24.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 25.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 26.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 27.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 28.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 29.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 30.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 31.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 32.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 33.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 32 steps 1.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 2.1: imidazole / dimethylformamide / 0 - 20 °C 3.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 4.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 5.2: tetrahydrofuran; hexane / 1 h / -30 °C 5.3: tetrahydrofuran; hexane / -20 °C 6.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 7.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 8.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 9.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 10.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 11.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 14.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 16.1: Et3N / benzene / 1 h / 20 °C 17.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 18.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 19.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 20.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 20.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: DMAP / pentane / 168 h / 20 °C 21.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 22.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 23.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 24.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 25.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 27.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 28.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 29.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 30.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 31.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 32.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 25 steps 1.1: 98 percent / K2CO3; MeOH / 2 h / 20 °C 2.1: imidazole / dimethylformamide / 0 - 20 °C 3.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C 4.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 5.2: tetrahydrofuran; hexane / 1 h / -30 °C 5.3: tetrahydrofuran; hexane / -20 °C 6.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C 7.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C 8.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C 9.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr 10.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C 11.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C 12.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 13.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 14.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 16.1: Et3N / benzene / 1 h / 20 °C 17.1: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 18.1: 93 percent / PPTS / ethanol / 10 h / 50 °C 19.1: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 20.1: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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714974-00-2
(1R,2R)-2-(((4-methoxybenzyl)oxy)methyl)cyclopentane-1-carbaldehyde
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7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 24 steps 1.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 2.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 4.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 5.1: 73 percent / benzene / 48 h / 80 °C 6.1: 84 percent / benzene / 39 h / 70 °C 7.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 8.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 9.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 10.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 11.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 11.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: DMAP / pentane / 168 h / 20 °C 12.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 13.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 15.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 16.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 17.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 23 steps 1.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 2.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 4.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 5.1: 73 percent / benzene / 48 h / 80 °C 6.1: 84 percent / benzene / 39 h / 70 °C 7.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 8.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 9.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 10.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 11.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 11.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12.1: DMAP / pentane / 168 h / 20 °C 12.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 13.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 14.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 15.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 16.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 17.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 19.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 20.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 23.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 16 steps 1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 2: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 3: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 4: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 5: 73 percent / benzene / 48 h / 80 °C 6: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 7: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 8: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 9: 93 percent / PPTS / ethanol / 10 h / 50 °C 10: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 11: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 12: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 13: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 14: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 16: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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714974-24-0
((1R,2R)-2-(((4-methoxybenzyl)oxy)methyl)cyclopentyl)methanol
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-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 25 steps 1.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 5.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 6.1: 73 percent / benzene / 48 h / 80 °C 7.1: 84 percent / benzene / 39 h / 70 °C 8.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 24 steps 1.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 5.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 6.1: 73 percent / benzene / 48 h / 80 °C 7.1: 84 percent / benzene / 39 h / 70 °C 8.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13.1: DMAP / pentane / 168 h / 20 °C 13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 17.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 17 steps 1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 2: 54 percent / tetrahydrofuran / 0.5 h / -78 °C 3: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 4: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 5: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 6: 73 percent / benzene / 48 h / 80 °C 7: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 8: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 10: 93 percent / PPTS / ethanol / 10 h / 50 °C 11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 12: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 13: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 14: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 15: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 17: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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714973-98-5
(2R,4S,6R,8S)-2,4,6,8-tetramethyl-9-(tetrahydro-2H-pyran-2-yloxy)nonanal
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-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 21 steps 1.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 2.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 4.1: Et3N / benzene / 1 h / 20 °C 5.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 6.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 8.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 8.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: DMAP / pentane / 168 h / 20 °C 9.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 10.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 12.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 13.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 14.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 20 steps 1.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 2.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 4.1: Et3N / benzene / 1 h / 20 °C 5.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 6.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 7.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 8.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 8.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 9.1: DMAP / pentane / 168 h / 20 °C 9.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 10.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 11.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 12.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 13.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 16.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 17.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 20.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 13 steps 1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 2: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 3: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 4: Et3N / benzene / 1 h / 20 °C 5: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 6: 93 percent / PPTS / ethanol / 10 h / 50 °C 7: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 8: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 9: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 10: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 11: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 12: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 13: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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714974-01-3
(+)-(S)-1-((1R,2R)-2-((4-methoxybenzyloxy)methyl)cyclopentyl)but-3-en-1-ol
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-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 23 steps 1.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 3.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 4.1: 73 percent / benzene / 48 h / 80 °C 5.1: 84 percent / benzene / 39 h / 70 °C 6.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 7.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 8.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 10.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 10.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: DMAP / pentane / 168 h / 20 °C 11.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 12.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 13.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 14.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 15.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 16.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 17.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 19.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 20.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 22.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 23.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 22 steps 1.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 3.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 4.1: 73 percent / benzene / 48 h / 80 °C 5.1: 84 percent / benzene / 39 h / 70 °C 6.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 7.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 8.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 9.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 10.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 10.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11.1: DMAP / pentane / 168 h / 20 °C 11.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 12.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 13.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 14.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 15.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 15 steps 1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 2: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 3: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 4: 73 percent / benzene / 48 h / 80 °C 5: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 6: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 7: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 8: 93 percent / PPTS / ethanol / 10 h / 50 °C 9: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 10: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 11: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 12: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 13: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 15: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
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714974-13-7
(-)-(2S,4S,6R,8S)-2,4,6,8-tetramethyl-9-(tetrahydro-2H-pyran-2-yloxy)nonan-1-ol
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-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 22 steps 1.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 3.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 5.1: Et3N / benzene / 1 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 21 steps 1.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 3.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 5.1: Et3N / benzene / 1 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 14 steps 1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 2: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C 3: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 4: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C 5: Et3N / benzene / 1 h / 20 °C 6: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 7: 93 percent / PPTS / ethanol / 10 h / 50 °C 8: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 10: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-16-0
(1'R,2'R,3S)-3-(tert-butyldimethylsilyloxy)-3-[2'-(4''-methoxybenzyloxymethyl)cyclopentyl]propanal
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 20 steps 1.1: 73 percent / benzene / 48 h / 80 °C 2.1: 84 percent / benzene / 39 h / 70 °C 3.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 4.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 5.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 6.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 7.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 7.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: DMAP / pentane / 168 h / 20 °C 8.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 9.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 11.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 12.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 13.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 15.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 16.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 17.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 19.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 20.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 19 steps 1.1: 73 percent / benzene / 48 h / 80 °C 2.1: 84 percent / benzene / 39 h / 70 °C 3.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 4.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 5.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 6.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 7.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 7.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 8.1: DMAP / pentane / 168 h / 20 °C 8.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 9.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 10.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 11.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 12.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 13.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 14.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 15.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 16.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 17.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 18.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 19.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 12 steps 1: 73 percent / benzene / 48 h / 80 °C 2: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 3: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 4: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 5: 93 percent / PPTS / ethanol / 10 h / 50 °C 6: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 7: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 8: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 9: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 10: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 11: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 12: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
-
-
714974-15-9
tert-butyl(((S)-1-((1R,2R)-2-(((4-methoxybenzyl)oxy)methyl)cyclopentyl)but-3-en-1-yl)oxy)dimethylsilane
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 22 steps 1.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 2.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 3.1: 73 percent / benzene / 48 h / 80 °C 4.1: 84 percent / benzene / 39 h / 70 °C 5.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C 16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 17.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 18.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 19.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 20.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 21.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 22.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 21 steps 1.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 2.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 3.1: 73 percent / benzene / 48 h / 80 °C 4.1: 84 percent / benzene / 39 h / 70 °C 5.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C 6.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C 7.1: 96 percent / PPTS / ethanol / 16 h / 50 °C 8.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: SmI2 / tetrahydrofuran / 1 h / -78 °C 9.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 10.1: DMAP / pentane / 168 h / 20 °C 10.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C 11.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C 12.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C 13.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C 14.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C 15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 16.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C 17.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 18.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 20.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 21.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme | |
| Multi-step reaction with 14 steps 1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C 2: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C 3: 73 percent / benzene / 48 h / 80 °C 4: 96 percent / DBU; LiCl / acetonitrile / 2 h / 0 °C 5: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C 6: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C 7: 93 percent / PPTS / ethanol / 10 h / 50 °C 8: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C 9: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C 10: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C 11: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C 12: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C 13: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C 14: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C View Scheme |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: piperazine In dichloromethane at 20℃; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: morpholine In dichloromethane at 20℃; | 96% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 93% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane | 91% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 1-phenylmethylpiperazine In dichloromethane at 20℃; | 90% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 89% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: piperidine In dichloromethane at 20℃; | 89% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; | 88% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 2-(aminoethyl)pyridine In dichloromethane at 20℃; | 88% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-Hydroxymethylpyridine In tetrahydrofuran at 20℃; | 88% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 1-methyl-piperazine In dichloromethane at 20℃; | 87% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 4-Methoxyphenethylamine In dichloromethane at 20℃; | 87% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 2-(5-methoxyindol-3-yl)ethylamine In dichloromethane at 20℃; | 86% |
Conditions
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid Reflux; | 85% |
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine; isobutyl chloroformate In tetrahydrofuran at 20℃; | 85% |
-
-
38212-30-5
1-(4-methoxyphenyl)piperazine
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 4-(4-methoxyphenyl)piperazine In dichloromethane at 20℃; | 85% |
-
-
39536-61-3
N-butylpentylamine
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: N-butylpentylamine In dichloromethane at 20℃; | 85% |
-
-
23032-21-5
D-leucine methyl ester
-
-
7184-60-3
borrelidin
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: D-leucine methyl ester In dichloromethane at 20℃; | 85% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 1-piperidinoethanol In tetrahydrofuran at 20℃; | 85% |
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine; isobutyl chloroformate In tetrahydrofuran at 20℃; | 84% |
-
-
622-40-2
2-(morpholin-4-yl)ethanol
-
-
7184-60-3
borrelidin
-
-
322480-23-9
2-morpholinoethyl (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S, 15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylate
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-(morpholin-4-yl)ethanol In tetrahydrofuran at 20℃; | 83% |
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane | 73% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: pyrrolidine In dichloromethane at 20℃; | 83% |
Conditions
| Conditions | Yield |
|---|---|
| In methanol; toluene at 20℃; | 82% |
Conditions
| Conditions | Yield |
|---|---|
| With triethylamine; isobutyl chloroformate In tetrahydrofuran at 20℃; | 82% |
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran at 20℃; for 0.5h; | 81% |
-
-
108-01-0
2-(N,N-dimethylamino)ethanol
-
-
7184-60-3
borrelidin
-
-
1429308-13-3
2-(dimethylamino)ethyl (1R,2R)-2-[(2S,4E,6Z,8R,9S, 11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetra-methyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylate
Conditions
| Conditions | Yield |
|---|---|
| With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane | 81% |
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-(N,N-dimethylamino)ethanol In tetrahydrofuran at 20℃; |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: 1-(2-hydroxyethyl)piperazine In dichloromethane at 20℃; | 80% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: borrelidin With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-phenylethanol In tetrahydrofuran at 20℃; | 80% |
Borrelidin Specification
The Borrelidin with CAS registry number of 7184-60-3 is also known as 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecar boxylic acid. The IUPAC name is (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid. In addition, the formula is C28H43NO6 and the molecular weight is 489.64. This chemical is a white to off-white powder and should be sealed in ventilated and dry place at the temperature of -20 °C.
Physical properties about Borrelidin are: (1)ACD/LogP: 4.31; (2)ACD/LogD (pH 5.5): 3.32; (3)ACD/LogD (pH 7.4): 1.52; (4)ACD/BCF (pH 5.5): 114.07; (5)ACD/BCF (pH 7.4): 1.79; (6)ACD/KOC (pH 5.5): 541.24; (7)ACD/KOC (pH 7.4): 8.51; (8)#H bond acceptors: 7; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.538; (12)Molar Refractivity: 133.52 cm3; (13)Molar Volume: 426.5 cm3; (14)Surface Tension: 50.4 dyne/cm; (15)Density: 1.14 g/cm3; (16)Flash Point: 383.4 °C; (17)Enthalpy of Vaporization: 118.69 kJ/mol; (18)Boiling Point: 710.3 °C at 760 mmHg; (19)Vapour Pressure: 2.6E-23 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
1. SMILES: O=C(O)[C@@H]1CCC[C@H]1[C@H]2OC(=O)C[C@H](O)[C@@H](C)C[C@@H](C)C[C@@H](C)C[C@@H]([C@@H](O)C(/C#N)=C\C=C\C2)C
2. InChI: InChI=1/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
3. InChIKey: OJCKRNPLOZHAOU-UGKRXNSEBA
4. Std. InChI: InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
5. Std. InChIKey: OJCKRNPLOZHAOU-UGKRXNSESA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| chicken | LD50 | intramuscular | 74mg/kg (74mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1198, 1978. | |
| mouse | LD50 | intravenous | 39mg/kg (39mg/kg) | Journal of Clinical Investigation. Vol. 28, Pg. 1047, 1949. | |
| mouse | LD50 | subcutaneous | 75mg/kg (75mg/kg) | Journal of Clinical Investigation. Vol. 28, Pg. 1047, 1949. | |
| rat | LD50 | intravenous | 2mg/kg (2mg/kg) | "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1198, 1978. | |
| rat | LD50 | subcutaneous | 1780ug/kg (1.78mg/kg) | Journal of Clinical Investigation. Vol. 28, Pg. 1047, 1949. |
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