Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 40℃; pH=9-9.8; | 99.33% |
With ammonia In dichloromethane; water at 25 - 35℃; | |
In dichloromethane; water at 37℃; pH=12; Product distribution / selectivity; | |
With ammonia In water at 35 - 70℃; for 1.5h; Reagent/catalyst; | 106 g |
Conditions | Yield |
---|---|
With hydrogen; Raney-Ni (W4) In ethanol at 25℃; for 1h; | 84% |
With hydrogen; Rany Ni (W4) In ethanol at 25℃; for 1h; | 84% |
(2',4''-O-bistrimethylsilyl)-6-O-methylerythromycinA-9[O-(1-ethoxy-1-methylethyl)]oxime
erythromycin
Conditions | Yield |
---|---|
With formic acid; water; sodium hydrogensulfite In ethanol for 8h; Heating; | 66.7% |
Conditions | Yield |
---|---|
With sodium cyanoborohydride In methanol; water for 0.5h; Ambient temperature; | A 11.4% B n/a |
Conditions | Yield |
---|---|
In methanol; water for 0.5h; Ambient temperature; | A 11.4% B n/a |
9-deoxo-9-iminoerythromycin A
erythromycin
Conditions | Yield |
---|---|
With water at 5℃; Yield given; | |
With water In methanol at 23℃; pH 7, methanol-phosphate buffer, various pH, other erythromycin; | |
With hydrogenchloride; water In ethanol pH=5 - 6; |
9-N,11-O-benzylidene-9-deoxo-9-iminoerythromycin A
erythromycin
Conditions | Yield |
---|---|
With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
C45H74N2O12
erythromycin
Conditions | Yield |
---|---|
With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
C44H71ClN2O12
erythromycin
Conditions | Yield |
---|---|
With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
C45H74N2O13
erythromycin
Conditions | Yield |
---|---|
With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
C44H71N3O14
erythromycin
Conditions | Yield |
---|---|
With water at 37℃; Rate constant; pH 7 (1:1 methanol-phosphate buffer); |
erythromycin A 9-(E)-oxime
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 30 percent / Bu3P / tetrahydrofuran / 1 h / 0 °C 2: H2O; HCl / ethanol / pH 5 - 6 View Scheme | |
Multi-step reaction with 2 steps 1.1: PySeSePy; Me3P / tetrahydrofuran / 0.17 h / 0 °C 1.2: 80 percent / H2O / pH 10 2.1: H2O; HCl / ethanol / pH 5 - 6 View Scheme |
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Bu3P / tetrahydrofuran / 1 h / 0 °C 2: H2O; HCl / ethanol / pH 5 - 6 View Scheme |
9S-Dihydroerythronolide A aglycon
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 87 percent / DL-10-camphorsulfonic acid / CH2Cl2 / 72 h / -30 °C 2: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 1.5 h / 25 °C 3: 95 percent / H2 / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C 4: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 5: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 6: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 7: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 8: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 9: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 10: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 11: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 11 steps 1: 87 percent / CSA / CH2Cl2 / 72 h / -30 °C 2: PPTS / CH2Cl2 / 1.5 h / 25 °C 3: H2 / Pd(OH)2 / 2 h / 25 °C 4: 63 percent / AgOTf, MS 4A / CH2Cl2; toluene / 4 h / 0 - 25 °C 5: 99 percent / mCPBA / CHCl3 / 0.33 h / 25 °C 6: 90 percent / NIS, TfOH, MS 4A / CH2Cl2 / 0.17 h / -35 °C 7: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 8: 54 percent / H2 / Raney-Ni (W4) / ethanol 9: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 10: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 11: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-9-dihydro-9,11-O-isopropylideneerythronolide A
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 2: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 3: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 4: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 5: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 6: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 7: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 8: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 8 steps 1: 63 percent / AgOTf, MS 4A / CH2Cl2; toluene / 4 h / 0 - 25 °C 2: 99 percent / mCPBA / CHCl3 / 0.33 h / 25 °C 3: 90 percent / NIS, TfOH, MS 4A / CH2Cl2 / 0.17 h / -35 °C 4: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 5: 54 percent / H2 / Raney-Ni (W4) / ethanol 6: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 7: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 8: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-9-dihydro-3,5-O-(p-methoxybenzylidene)erythronolide A
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 100 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 1.5 h / 25 °C 2: 95 percent / H2 / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C 3: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 4: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 5: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 6: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 7: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 8: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 9: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 10: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 10 steps 1: PPTS / CH2Cl2 / 1.5 h / 25 °C 2: H2 / Pd(OH)2 / 2 h / 25 °C 3: 63 percent / AgOTf, MS 4A / CH2Cl2; toluene / 4 h / 0 - 25 °C 4: 99 percent / mCPBA / CHCl3 / 0.33 h / 25 °C 5: 90 percent / NIS, TfOH, MS 4A / CH2Cl2 / 0.17 h / -35 °C 6: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 7: 54 percent / H2 / Raney-Ni (W4) / ethanol 8: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 9: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 10: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-9-dihydro-9,11-O-isopropylidene-3,5-O-(p-methoxybenzylidene)erythronolide
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 95 percent / H2 / Pd(OH)2/C / ethyl acetate / 2 h / 25 °C 2: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 3: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 4: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 5: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 6: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 7: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 8: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 9: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 9 steps 1: H2 / Pd(OH)2 / 2 h / 25 °C 2: 63 percent / AgOTf, MS 4A / CH2Cl2; toluene / 4 h / 0 - 25 °C 3: 99 percent / mCPBA / CHCl3 / 0.33 h / 25 °C 4: 90 percent / NIS, TfOH, MS 4A / CH2Cl2 / 0.17 h / -35 °C 5: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 6: 54 percent / H2 / Raney-Ni (W4) / ethanol 7: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 8: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 9: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 2: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 3: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 4: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 5: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 6: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 7: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 7 steps 1: 99 percent / mCPBA / CHCl3 / 0.33 h / 25 °C 2: 90 percent / NIS, TfOH, MS 4A / CH2Cl2 / 0.17 h / -35 °C 3: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 4: 54 percent / H2 / Raney-Ni (W4) / ethanol 5: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 6: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 7: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-oxide
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 2: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 3: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 4: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 5: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 6: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 6 steps 1: 90 percent / NIS, TfOH, MS 4A / CH2Cl2 / 0.17 h / -35 °C 2: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 3: 54 percent / H2 / Raney-Ni (W4) / ethanol 4: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 5: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 6: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-9-dihydroerythromycin A N-oxide
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 2: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 2: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 2: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 3: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 4: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 4 steps 1: 54 percent / H2 / Raney-Ni (W4) / ethanol 2: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 3: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 4: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 2: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 3: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 4: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 5: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 5 steps 1: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 2: 54 percent / H2 / Raney-Ni (W4) / ethanol 3: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 4: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 5: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranoside
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 91 percent / TMSOTf / CH2Cl2 / 0.25 h / 0 °C 2: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 3: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 4: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 5: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 6: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 7: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 7 steps 1: 96 percent / TMSOTf / CH2Cl2 / 0.17 h / -10 °C 2: 90 percent / NIS, TfOH, MS 4A / CH2Cl2 / 0.17 h / -35 °C 3: 66 percent / 50percent aq. AcOH / 24 h / 40 °C 4: 54 percent / H2 / Raney-Ni (W4) / ethanol 5: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 6: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 7: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-β-L-altro-pyranoside
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 2: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 3: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 4: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 5: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 6: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
1-(2-pyrimidinethio) 3,4,6-trideoxy-2-O-methoxycarbonyl-3-(dimethylamino)-D-xylo-hexopyranoside
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 63 percent / silver triflate, 4A molecular sieves / CH2Cl2; toluene / 4 h / 25 °C 2: 100 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.25 h / 25 °C 3: 90 percent / 4A molecular sieves, N-iodosuccinimide, TfOH / CH2Cl2 / 0.17 h / -35 °C 4: 66 percent / 50percent aq. AcOH / 12 h / 40 °C 5: 54 percent / H2 / Raney Ni (W4) / ethanol / 1.5 h / 40 °C 6: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 7: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 8: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
(9S)-9-dihydroerythromycin A
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 99 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 0.17 h / 25 °C 2: 58 percent / bis(tri-n-butyltin) oxide, Br2 / CH2Cl2 / 24 h / 25 °C 3: 84 percent / H2 / Rany Ni (W4) / ethanol / 1 h / 25 °C View Scheme | |
Multi-step reaction with 3 steps 1: 99 percent / mCPBA / CHCl3 / 0.17 h / 25 °C 2: 58 percent / (n-Bu3Sn)2O, Br2 / CH2Cl2 / 24 h / 25 °C 3: 84 percent / H2 / Raney-Ni (W4) / ethanol / 1 h / 25 °C View Scheme |
D-desosamine
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: (NCO2Et)2, P(n-Bu)3 / toluene / -30 - 25 °C 2: aq. NaHCO3 / CH2Cl2 / 25 °C 3: silver triflate / CH2Cl2; toluene / 25 °C 4: Pb(ClO4)2 / acetonitrile / 25 °C 5: MeOH 6: 75 percent / Na-Hg/MeOH 7: N-chlorosuccinimide / pyridine / 25 °C 8: AgF / hexamethylphosphoric acid triamide / 70 °C 9: H2O / 5 °C View Scheme |
4-acetyl-L-cladinose
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 72 percent / P(n-Bu)3 / CH2Cl2 / 0 °C 2: Pb(ClO4)2 / acetonitrile / 25 °C 3: MeOH 4: 75 percent / Na-Hg/MeOH 5: N-chlorosuccinimide / pyridine / 25 °C 6: AgF / hexamethylphosphoric acid triamide / 70 °C 7: H2O / 5 °C View Scheme |
erythromycylamine
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-chlorosuccinimide / pyridine / 25 °C 2: AgF / hexamethylphosphoric acid triamide / 70 °C 3: H2O / 5 °C View Scheme |
4-O-acetyl-1-deoxy-1-(2-pyridylthio)-α-L-cladinoside
erythromycin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Pb(ClO4)2 / acetonitrile / 25 °C 2: MeOH 3: 75 percent / Na-Hg/MeOH 4: N-chlorosuccinimide / pyridine / 25 °C 5: AgF / hexamethylphosphoric acid triamide / 70 °C 6: H2O / 5 °C View Scheme |
succinic acid anhydride
erythromycin
2'-O-(3-carboxypropanoyl) erythromycin
Conditions | Yield |
---|---|
In acetone at 50℃; | 100% |
With acetone | |
With dichloromethane |
erythromycin
erythromycin A 9-(E)-oxime
Conditions | Yield |
---|---|
With hydroxylamine; acetic acid In water; isopropyl alcohol at 50℃; for 15h; Inert atmosphere; | 100% |
With hydroxylamine hydrochloride; sodium acetate; acetic acid In methanol at 55℃; for 24h; | 98% |
With hydroxylamine hydrochloride; triethylamine In methanol for 96h; Heating / reflux; | 84% |
erythromycin
lactobionic acid
erythromycin lactobionate
Conditions | Yield |
---|---|
With water at 5 - 40℃; Product distribution / selectivity; | 99% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In methanol; water at 15 - 20℃; for 20h; | 98% |
With dihydrogen peroxide In methanol; water at 20℃; for 19h; | 90% |
With dihydrogen peroxide In methanol at 20℃; | 88% |
With sodium periodate; ethanol; water | |
With dihydrogen peroxide |
erythromycin
(9-E)-deoxo-9-hydroximinoerythromycin A
Conditions | Yield |
---|---|
With hydroxylamine; acetic acid In isopropyl alcohol at 50℃; for 24h; | 95% |
With hydroxylamine hydrochloride; triethylamine In methanol Reflux; | 93% |
With hydroxylamine hydrochloride; potassium carbonate In methanol at 20℃; for 48h; Solvent; Reagent/catalyst; Temperature; | 88.2% |
2-Methoxypropene
erythromycin
11,12-isopropylidene-8,9-anhydroerythromycin A 6,9-hemiacetal
Conditions | Yield |
---|---|
With pyridine hydrochloride In chloroform for 24h; Ambient temperature; | 94% |
ethanol
erythromycin
(2S,3S,4R,6S)-6-Ethoxy-4-methoxy-2,4-dimethyl-tetrahydro-pyran-3-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetonitrile for 1h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With pyridine In ethyl acetate at 20℃; for 1h; | 91% |
In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; | 66% |
In dichloromethane at 20℃; | |
With 1-methyl-1H-imidazole | |
In dichloromethane |
erythromycin
(9S)-9-dihydroerythromycin A
Conditions | Yield |
---|---|
Stage #1: erythromycin With sodium tetrahydroborate In diethyl ether; isopropyl alcohol at 0 - 20℃; for 3h; Stage #2: With triethanolamine In diethyl ether; water; isopropyl alcohol for 2h; pH=6.5; Product distribution / selectivity; | 86% |
With sodium tetrahydroborate In diethyl ether; isopropyl alcohol at 0 - 20℃; | 86% |
With aluminum oxide; sodium tetrahydroborate | 82% |
Conditions | Yield |
---|---|
Stage #1: erythromycin In acetone at 35℃; pH=8.5; Stage #2: sodium thiocyanide In acetone Concentration; pH-value; Temperature; Solvent; | 85.1% |
Stage #1: erythromycin With LACTIC ACID; water at 5 - 40℃; Stage #2: sodium thiocyanide In water at -15 - 10℃; Product distribution / selectivity; | |
Stage #1: erythromycin In acetone at 35℃; pH=8.5; Stage #2: sodium thiocyanide In acetone | 85.1 %Chromat. |
Conditions | Yield |
---|---|
With sodium hydroxide; iodine; sodium acetate In methanol; water at 20 - 50℃; for 3.5h; pH=8 - 9; | 84% |
With iodine; sodium acetate In methanol; water | 34% |
With sodium hydroxide; iodine; sodium acetate In methanol; water for 2.5h; |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; | 84% |
erythromycin
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; pH=1.7; | 81% |
prop-2-yn-1-ol methanesulfonate
tert-butyl 2-azidoacetate
erythromycin
CH3O3S(1-)*C46H81N4O15(1+)
Conditions | Yield |
---|---|
80% |
benzyl chloroformate
erythromycin
B
2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A
Conditions | Yield |
---|---|
With sodium hydrogencarbonate at 50℃; for 1h; | A n/a B 79% |
C21H36O4
erythromycin
A
2'-O-linoleoylerythromycin A
B
4''-O-linoleoylerythromycin A
C
erythromycin, 2'-(ethyl carbonate)
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 20℃; for 10h; | A 78% B n/a C 5% |
benzyl chloroformate
erythromycin
2'-O,3'-N-bis(benzyloxycarbonyl)-N-demethylerythromycin A
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In toluene | 77% |
With sodium hydrogencarbonate |
chloro-trimethyl-silane
erythromycin
2',4''-O-Bis(trimethylsilyl)erythromycin A
Conditions | Yield |
---|---|
With 1-(Trimethylsilyl)imidazole In ethyl acetate for 0.5h; Ambient temperature; | 76% |
erythromycin
phenylcarbonochloridothioate
erythromycin A-2'-phenylthionoformate
Conditions | Yield |
---|---|
With 1,2,2,6,6-pentamethylpiperidine; 1-methyl-1H-imidazole In dichloromethane at 20℃; for 2h; | 76% |
With triethylamine |
methanesulfonyl chloride
erythromycin
2',4''-di-O-methanesulfonylerythromycin A
Conditions | Yield |
---|---|
With triethylamine In acetone 1.) 0 to 3 deg C, 30 min, 2.) RT, 2 h; | 75.7% |
erythromycin
Conditions | Yield |
---|---|
With glycosyltransferase OleD; Tris buffer at 37℃; pH=7.8; | 74% |
Conditions | Yield |
---|---|
With C47H62N8O10; triethylamine In chloroform Inert atmosphere; | A 71% B n/a |
With pyridine Title compound not separated from byproducts.; |
erythromycin
EM 201
Conditions | Yield |
---|---|
With acetic acid at 20℃; for 2h; | 71% |
Product distribution / selectivity; Acidic aqueous solution; |
Conditions | Yield |
---|---|
With pyridine at 25℃; for 72h; | A 70% B n/a |
erythromycin
8,9-anhydroerythromycin A 6,9-hemiacetal
Conditions | Yield |
---|---|
With acetic acid for 1h; Ambient temperature; | 68% |
With acetic acid Erwaermen bei vermindertem Druck; | |
With acetic acid at 20℃; | |
With acetic acid at 20℃; for 0.75h; |
erythromycin
3-tert-butoxycarbonylamino-propionic acid anhydride
C
C53H93N3O19
Conditions | Yield |
---|---|
With C47H62N8O10; triethylamine In chloroform at 20℃; for 65h; Inert atmosphere; | A 13% B 3% C 68% |
erythromycin
3-tert-butoxycarbonylamino-propionic acid anhydride
B
C53H93N3O19
Conditions | Yield |
---|---|
With C47H62N8O10; triethylamine In chloroform Inert atmosphere; | A n/a B 68% |
1、Lilly filed for patent protection of the compound and U.S. patent 2,653,899 was granted in 1953. The product was launched commercially in 1952 under the brand name Ilosone.
2、In 1981, Nobel laureate (1965 in chemistry) and Professor of Chemistry at Harvard University (Cambridge, MA) Robert B. Woodward, along with a large number of members from his research group, posthumously reported the first stereocontrolled asymmetric chemical synthesis of Erythromycin A.
3、The antiobiotic clarithromycin was invented by scientists at the Japanese drug company Taisho Pharmaceutical in the 1970s as a result of their efforts to overcome the acid instability ofErythromycin (CAS NO.114-07-8).
4、Presently, Erythromycin (CAS NO.114-07-8) is commonly used off-label for gastric motility indications such as Gastroparesis.
EPA Genetic Toxicology Program.
The Erythromycin, with the CAS registry number 114-07-8, is also known as Abboticin. It belongs to the product categories of Antibiotics; Organics; Antibiotics for Research and Experimental Use; Biochemistry; Macrolides (Antibiotics for Research and Experimental Use); Antibiotic Explorer; Intermediates & Fine Chemicals; Pharmaceuticals; Immune System Regulation; MacrolidesMore...Close...; Antibiotics A-FAlphabetic; EQ - EZAntibiotics; Chemical Structure Class; Core Bioreagents; Interferes with Protein Synthesis Antibiotics; Mechanism of Action; Pharmacopoeia A-ZPharmacopoeia (USP); Spectrum of Activity; Macrolides; A - KCell Culture; Reagents and Supplements; API's. Its EINECS number is 204-040-1. This chemical's molecular formula is C37H67NO13 and molecular weight is 733.93. What's more, its systematic name is (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(Dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethylte trahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione. Its classification codes are: (1)Anti-Bacterial Agents; (2)Anti-Infective Agents; (3)Antibacterial; (4)Drug / Therapeutic Agent; (5)Enzyme Inhibitors; (6)Gastrointestinal agents; (7)Human Data; (8)Mutation data; (9)Natural Product; (10)Protein synthesis inhibitors; (11)Reproductive Effect. This chemical is a macrolide antibiotic that has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often used for people who have an allergy to penicillins. Erythromycin is available in enteric-coated tablets, slow-release capsules, oral suspensions, ophthalmic solutions, ointments, gels, and injections.
Physical properties of Erythromycin are: (1)ACD/LogP: 1.909; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -0.54; (4)ACD/LogD (pH 7.4): 1.16; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 2.98; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 46.71; (9)#H bond acceptors: 14; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 193.91 Å2; (13)Index of Refraction: 1.535; (14)Molar Refractivity: 189.169 cm3; (15)Molar Volume: 607.183 cm3; (16)Polarizability: 74.992×10-24cm3; (17)Surface Tension: 51.42 dyne/cm; (18)Density: 1.209 g/cm3; (19)Flash Point: 448.753 °C; (20)Enthalpy of Vaporization: 135.404 kJ/mol; (21)Boiling Point: 818.401 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Preparation: it is a kind of Alkaline antibiotics extracted from culture solution of Streptomyces erythreus. During the process of purification, use butyl acetate and aqueous solution to ectract again and again to achieve the purpose of concentration purification. Finally, the products are got by freezing crystallization in the solution of butyl acetate.
Uses of Erythromycin: it can be used to produce pseudoerythromycin A enol ether and erythromycin A enol ether at the temperature of 70 °C. It will need reagents pyridine, acetic acid with the reaction time of 24 hours. The yield is about 71%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It may cause sensitisation by inhalation and skin contact. You must avoid contact with skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing and gloves. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
(2)Std. InChI: InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
(3)Std. InChIKey: ULGZDMOVFRHVEP-RWJQBGPGSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | oral | 10mg/kg/1D-I (10mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Annals of Internal Medicine. Vol. 115, Pg. 69, 1991. |
child | TDLo | oral | 250mg/kg (250mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: OTHER CHANGES BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT | Pediatrics. Vol. 90, Pg. 624, 1992. |
dog | LDLo | unreported | > 100mg/kg (100mg/kg) | Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952. | |
guinea pig | LD50 | intraperitoneal | 413mg/kg (413mg/kg) | Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952. | |
hamster | LD50 | oral | 3018mg/kg (3018mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 41, Pg. 555, 1952. |
mouse | LD50 | intramuscular | 394mg/kg (394mg/kg) | Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 44, Pg. 199, 1955. | |
mouse | LD50 | intraperitoneal | 280mg/kg (280mg/kg) | Journal of Antibiotics. Vol. 43, Pg. 938, 1990. | |
mouse | LD50 | intravenous | 426mg/kg (426mg/kg) | "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 273, 1967. | |
mouse | LD50 | oral | 2580mg/kg (2580mg/kg) | Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974. | |
mouse | LD50 | subcutaneous | 1800mg/kg (1800mg/kg) | Antibiotics and Chemotherapy Vol. 2, Pg. 281, 1952. | |
rat | LD50 | oral | 4600mg/kg (4600mg/kg) | Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 31, Pg. 241, 1974. | |
rat | LDLo | subcutaneous | 427mg/kg (427mg/kg) | Compilation of LD50 Values of New Drugs. |
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