3-Benzyloxy-pyridine-2-carboxylic acid {(5R,6S,9S,10S,11R)-10-hydroxy-5,11-dimethyl-2-[1-methyl-prop-(Z)-ylidene]-3,7,12-trioxo-9-pyridin-3-ylmethyl-1,4-dioxa-8-aza-cyclododec-6-yl}-amide
pyridomicin
Conditions | Yield |
---|---|
With hydrogen; palladium In methanol | 95% |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1: NaIO4, RuCl3 / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 2: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature 3: aq. TFA / 1 h / Ambient temperature 4: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature 5: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 6: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 7: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 8: DCC, HOBt / dimethylformamide / 68 h / 2 °C 9: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 10: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 11: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 12: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 13: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 15: 95 percent / H2 / Pd-black / methanol View Scheme |
(R)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature 2: aq. TFA / 1 h / Ambient temperature 3: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature 4: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 5: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 6: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 7: DCC, HOBt / dimethylformamide / 68 h / 2 °C 8: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 9: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 10: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 11: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 12: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 14: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 17 steps 1: DMP, H2SO4 / 2 h / Ambient temperature 2: H2 / Pd(OH)2 / methanol / 1 h / Ambient temperature 3: NaIO4, RuCl3 / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 4: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature 5: aq. TFA / 1 h / Ambient temperature 6: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature 7: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 8: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 9: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 10: DCC, HOBt / dimethylformamide / 68 h / 2 °C 11: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 12: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 13: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 14: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 15: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 17: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1: H2 / Pd(OH)2 / methanol / 1 h / Ambient temperature 2: NaIO4, RuCl3 / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 3: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature 4: aq. TFA / 1 h / Ambient temperature 5: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature 6: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 7: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 8: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 9: DCC, HOBt / dimethylformamide / 68 h / 2 °C 10: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 11: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 12: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 13: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 14: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 16: 95 percent / H2 / Pd-black / methanol View Scheme |
(S)-1-Benzyloxy-3-ethyl-2-methoxymethoxy-pentan-3-ol
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 18 steps 1: aq. HCl / dioxane / 3 h / 50 °C 2: DMP, H2SO4 / 2 h / Ambient temperature 3: H2 / Pd(OH)2 / methanol / 1 h / Ambient temperature 4: NaIO4, RuCl3 / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 5: 83 percent / DCC,DMAP / ethyl acetate / 2 h / Ambient temperature 6: aq. TFA / 1 h / Ambient temperature 7: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature 8: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 9: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 10: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 11: DCC, HOBt / dimethylformamide / 68 h / 2 °C 12: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 13: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 14: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 15: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 16: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 18: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature 2: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 3: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 4: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 5: DCC, HOBt / dimethylformamide / 68 h / 2 °C 6: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 7: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 8: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 9: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 10: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 12: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 95 percent / H2 / Pd-black / methanol View Scheme |
(R)-3-Ethyl-2,3-dihydroxy-pentanoic acid (1R,2S)-2-benzhydryloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethyl ester
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 2: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 3: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 4: DCC, HOBt / dimethylformamide / 68 h / 2 °C 5: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 6: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 7: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 8: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 9: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 11: 95 percent / H2 / Pd-black / methanol View Scheme |
(R)-5,5-Diethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid (1R,2S)-2-benzhydryloxycarbonyl-2-benzyloxycarbonylamino-1-methyl-ethyl ester
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: aq. TFA / 1 h / Ambient temperature 2: ethyl acetate; petroleum ether / 2.5 h / Ambient temperature 3: DCC, DMAP / ethyl acetate / 2.5 h / Ambient temperature 4: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 5: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 6: DCC, HOBt / dimethylformamide / 68 h / 2 °C 7: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 8: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 9: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 10: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 11: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 13: 95 percent / H2 / Pd-black / methanol View Scheme |
[(2R,5R,6S,9S,10S,11R)-2-((E)-1-Ethyl-propenyl)-10-hydroxy-5,11-dimethyl-3,7,12-trioxo-9-pyridin-3-ylmethyl-1,4-dioxa-8-aza-cyclododec-6-yl]-carbamic acid benzyl ester
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 2: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 3: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 4: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 6: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 2: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 3: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 4: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 5: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 7: 95 percent / H2 / Pd-black / methanol View Scheme |
{(5R,6S,9S,10S,11R)-10-Hydroxy-5,11-dimethyl-2-[1-methyl-prop-(Z)-ylidene]-3,7,12-trioxo-9-pyridin-3-ylmethyl-1,4-dioxa-8-aza-cyclododec-6-yl}-carbamic acid benzyl ester
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 3: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: DCC, HOBt / dimethylformamide / 68 h / 2 °C 2: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 3: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 4: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 5: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 6: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 8: 95 percent / H2 / Pd-black / methanol View Scheme |
((5R,6S,9S,10S,11R)-10-Hydroxy-5,11-dimethyl-3,7,12-trioxo-2-propionyl-9-pyridin-3-ylmethyl-1,4-dioxa-8-aza-cyclododec-6-yl)-carbamic acid benzyl ester
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 2: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 3: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 5: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 2: DCC, HOBt / dimethylformamide / 68 h / 2 °C 3: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 4: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 5: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 6: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 7: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 9: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 2: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 4: 95 percent / H2 / Pd-black / methanol View Scheme |
pyridomicin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 1.) aq. HCl 2.) aq. TFA / 1 ) dioxane, 35 deg C, 12 h 2 ) rt., 20 min. 2: H2 / Raney-Ni W-4 / methanol / 0.67 h / 35 °C 3: DCC, HOBt / dimethylformamide / 68 h / 2 °C 4: 95 percent / SOCl2 / pyridine / 1 h / -30 °C 5: 84 percent / O3/O2 / CH2Cl2 / 0 h / -78 °C 6: 1)NaH / 1)THF, 0 deg C, 15 min., 2)0 deg C, 1 h 7: 25 percent / tetrahydrofuran / 3 h / -70 - -30 °C 8: H2 / Pd-black / methanol / 0.5 h / Ambient temperature 10: 95 percent / H2 / Pd-black / methanol View Scheme |
IUPAC Name: N-[(1S,4S,5R,6R,9Z,12R)-9-Butan-2-ylidene-5-hydroxy-6,12-dimethyl-2,7,10-trioxo-4-(pyridin-3-ylmethyl)-8,11-dioxa-3-azacyclododec-1-yl]-3-hydroxypyridine-2-carboxamide
Synonyms: [5R-(2Z,5R*,6S*,9S*,10S*,11R*)]-3-Hydroxy-N-[10-hydroxy-5,11-dimethyl-2-(1-methylpropylidene)-3,7,12-trioxo-9-(3-pyridinylmethyl)-1,4-dioxa-8-azacyclododec-6-yl]-2-pyridinecarboxamide ; Pyridomycin
CAS NO: 18791-21-4
Molecular Formula of Pyridomycin (CAS NO.18791-21-4) : C27H32N4O8
Molecular Weight of Pyridomycin (CAS NO.18791-21-4) : 540.565
Molecular Structure of Pyridomycin (CAS NO.18791-21-4) :
Index of Refraction: 1.606
Surface Tension: 67.3 dyne/cm
Density: 1.35 g/cm3
Flash Point: 529 °C
Enthalpy of Vaporization: 145.04 kJ/mol
Boiling Point: 951.1 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
1. | orl-mus LD50:1000 mg/kg | 85GDA2 CRC Handbook of Antibiotic Compounds, Volumes 1-9. 4 (2)(1980),144. | ||
2. | ipr-mus LD50:1000 mg/kg | 85GDA2 CRC Handbook of Antibiotic Compounds, Volumes 1-9. 4 (2)(1980),144. | ||
3. | ivn-mus LD50:300 mg/kg | 85FZAT Index of Antibiotics from Actinomycetes Umezawa, H., et al., eds.,Tokyo, Japan.: University of Tokyo Press,1967,541. |
Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.
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