2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate

Base Information

• Chemical Name: 2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate
• CAS No.: 113792-83-9
• Molecular Formula: C₄₉H₇₅NO₁₇
• Molecular Weight: 950.131
• Mol file: 113792-83-9.mol

Synonyms:2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate

Chemical Property of 2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate

There total 3 articles about 2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate 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:

clarithromycin (81103-11-9) → 2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate (113792-83-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / triethylamine / CH₂Cl₂ / 5.5 h

2: 87 percent / (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1.) -40 deg C, 1 h, 2.) -20 deg C, 72 h

3: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -35 deg C, 10 min, 2.) RT, 15 min

With dmap; sodium hexamethyldisilazane; triethylamine; In dichloromethane;

DOI:10.1021/jo00245a038

Reference yield:

2'-O-acetyl-6-O-methylerythromycin A (103461-66-1) → 2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate (113792-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1.) -40 deg C, 1 h, 2.) -20 deg C, 72 h

2: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -35 deg C, 10 min, 2.) RT, 15 min

With dmap; sodium hexamethyldisilazane; In dichloromethane;

DOI:10.1021/jo00245a038

Reference yield:

2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A (113777-91-6) + 1,1'-carbonyldiimidazole (530-62-1) → 2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-carbonate (113792-83-9)

Guidance literature:

With sodium hexamethyldisilazane; Yield given. Multistep reaction; 1.) THF, -35 deg C, 10 min, 2.) RT, 15 min;

DOI:10.1021/jo00245a038

upstream raw materials:

2'-O-acetyl-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A

1,1'-carbonyldiimidazole

clarithromycin

2'-O-acetyl-6-O-methylerythromycin A

Downstream raw materials:

C₄₇H₇₄N₂O₁₅

C₄₉H₇₆N₂O₁₆

2'-O-Acetyl-11-deoxy-11-(carboxyamino)-4''-O-(benzyloxycarbonyl)-6-O-methylerythromycin A 11,12-(cyclic ester)

2'-O-acetyl-4''-O-(benzyloxycarbonyl)-10,11-didehydro-6-O-methylerythromycin A