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CAS No.: | 205110-48-1 |
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Name: | Cethromycin |
Article Data: | 1 |
Molecular Structure: | |
Formula: | C42H59N3O10 |
Molecular Weight: | 765.945 |
Synonyms: | Cethromycin;ABT 773;Restanza; |
Density: | 1.22g/cm3 |
Melting Point: | 211-213° |
Boiling Point: | 927.1°Cat760mmHg |
Flash Point: | 514.5°C |
PSA: | 162.82000 |
LogP: | 5.43850 |
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
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Multi-step reaction with 8 steps 1.1: sodium hydrogensulfite; formic acid / water; ethanol / 2.5 h / 86 °C 2.1: dmap / dichloromethane / 3 h / 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 3.2: 28 h / -40 - 20 °C / Inert atmosphere 4.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / water; ethanol / 22 h 6.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 6.2: 1 h / 10 °C / Inert atmosphere 7.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 8.1: methanol / Reflux View Scheme |
acetic acid 2-[4-(5-acetoxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-7-allyloxy-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-6-yloxy]-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 1.2: 28 h / -40 - 20 °C / Inert atmosphere 2.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride / water; ethanol / 22 h 4.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 4.2: 1 h / 10 °C / Inert atmosphere 5.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 6.1: methanol / Reflux View Scheme |
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere 2.1: hydrogenchloride / water; ethanol / 22 h 3.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 3.2: 1 h / 10 °C / Inert atmosphere 4.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 5.1: methanol / Reflux View Scheme |
2',4"-O-diacetyl-6-O-allyl-11,12-cyclocarbamate erythromycin A
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water; ethanol / 22 h 2.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 2.2: 1 h / 10 °C / Inert atmosphere 3.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 4.1: methanol / Reflux View Scheme |
acetic acid 2-(11-allyloxy-4-ethyl-8-hydroxy-3a,7,9,11,13,15-hexamethyl-2,6,14-trioxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 1.2: 1 h / 10 °C / Inert atmosphere 2.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 3.1: methanol / Reflux View Scheme |
acetic acid 2-(11-allyloxy-4-ethyl-3a,7,9,11,13,15-hexamethyl-2,6,8,14-tetraoxo-tetradecahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecen-10-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 2: methanol / Reflux View Scheme |
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
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With methanol Reflux; | 32.95 g |
6-O-allylerythromycin A
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: dmap / dichloromethane / 3 h / 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 2.2: 28 h / -40 - 20 °C / Inert atmosphere 3.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / water; ethanol / 22 h 5.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 5.2: 1 h / 10 °C / Inert atmosphere 6.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 7.1: methanol / Reflux View Scheme |
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: acetic acid / acetonitrile; water / 20 °C 2.1: sodium hydrogensulfite; formic acid / water; ethanol / 2.5 h / 86 °C 3.1: dmap / dichloromethane / 3 h / 20 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 4.2: 28 h / -40 - 20 °C / Inert atmosphere 5.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere 6.1: hydrogenchloride / water; ethanol / 22 h 7.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 7.2: 1 h / 10 °C / Inert atmosphere 8.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 9.1: methanol / Reflux View Scheme |
10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-4-ethyl-3a,7,9,11,13,15-hexamethyl-11-(3-quinolin-3-yl-allyloxy)-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone
Conditions | Yield |
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Multi-step reaction with 10 steps 1.1: potassium tert-butylate / dimethyl sulfoxide; tetrahydrofuran / 4 h / 0 °C 2.1: acetic acid / acetonitrile; water / 20 °C 3.1: sodium hydrogensulfite; formic acid / water; ethanol / 2.5 h / 86 °C 4.1: dmap / dichloromethane / 3 h / 20 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere 5.2: 28 h / -40 - 20 °C / Inert atmosphere 6.1: ammonium hydroxide / tetrahydrofuran; acetonitrile / 192 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / water; ethanol / 22 h 8.1: N-chloro-succinimide; dimethylsulfide / dichloromethane / 0.5 h / -10 - -5 °C / Inert atmosphere 8.2: 1 h / 10 °C / Inert atmosphere 9.1: triethylamine; palladium diacetate; tris-(o-tolyl)phosphine / acetonitrile / 97 h / 50 - 90 °C / Inert atmosphere 10.1: methanol / Reflux View Scheme |