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205110-48-1

Basic Information
CAS No.: 205110-48-1
Name: Cethromycin
Article Data: 1
Molecular Structure:
Molecular Structure of 205110-48-1 (Cethromycin)
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
Synthetic route

C40H72N2O13

205110-48-1

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
ConditionsYield
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
198557-85-6

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

205110-48-1

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
ConditionsYield
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

C48H75N3O15

205110-48-1

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
ConditionsYield
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
198557-87-8

2',4"-O-diacetyl-6-O-allyl-11,12-cyclocarbamate erythromycin A

205110-48-1

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
ConditionsYield
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
205110-77-6

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

205110-48-1

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
ConditionsYield
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
205110-78-7

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

205110-48-1

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
ConditionsYield
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

C44H61N3O11

205110-48-1

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
ConditionsYield
With methanol Reflux;32.95 g
198482-51-8

6-O-allylerythromycin A

205110-48-1

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
ConditionsYield
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

C55H104N2O14Si2

205110-48-1

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
ConditionsYield
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

2',4"-bis-O-trimethylsilylerythromycin A 9-O-(1-isopropoxycyclohexyl)oxime

205110-48-1

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
ConditionsYield
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
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