[10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester
• CAS No.: 79617-15-5
• Molecular Formula: C₄₅H₇₆N₂O₁₄
• Molecular Weight: 869.103
• Mol file: 79617-15-5.mol

Synonyms:[10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester

Chemical Property of [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester

There total 5 articles about [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.29%

erythromycylamine (26116-56-3) + benzyl chloroformate (501-53-1,94274-21-2) → [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester (79617-15-5)

Guidance literature:

In dichloromethane; at 40 ℃; for 12h; Solvent; Temperature; Cooling with ice;

Reference yield:

erythromycylamine (26116-56-3) → [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester (79617-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / chloroform; water / 1 h / 0 °C

2: methanol / 18 h / Reflux

With sodium hydrogencarbonate; In methanol; chloroform; water;

DOI:10.1016/j.bmc.2012.08.007

Reference yield:

(9-E)-deoxo-9-hydroximinoerythromycin A (13127-18-9) → [10-(4-dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,4,9-trihydroxy-12-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-14-oxo-oxacyclotetradec-6-yl]-carbamic acid benzyl ester (79617-15-5)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; sodium tetrahydroborate / 8 h / 20 °C / Cooling with ice

2: dichloromethane / 12 h / 40 °C / Cooling with ice

With methanol; sodium tetrahydroborate; In dichloromethane;

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

erythromycylamine

benzyl chloroformate

(9-E)-deoxo-9-hydroximinoerythromycin A

Downstream raw materials:

C₄₉H₇₇N₅O₁₄

C₅₉H₉₅N₅O₁₅

C₄₉H₈₇N₅O₁₂

C₆₀H₁₁₁N₃O₁₄Si₂