(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester

Base Information

• Chemical Name: (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester
• CAS No.: 302784-48-1
• Molecular Formula: C₅₂H₇₉N₃O₁₄
• Molecular Weight: 970.211
• Mol file: 302784-48-1.mol

Synonyms:(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester

Chemical Property of (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester

There total 5 articles about (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic 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: 92.0%

BOC-glycine (4530-20-5) + benzyl 3α,7α,12α-trihydroxyl-5β-cholestane-24-carboxylic ester (105730-97-0) → (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester (302784-48-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 25 ℃; for 12h;

DOI:10.1021/acs.jmedchem.8b01357

Reference yield:

cholic acid (81-25-4) → (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester (302784-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / 10-camphorsulfonic acid / 16 h / 20 °C / vacuum

2: 68 percent / DCC; DMAP / CH₂Cl₂ / 16 h

With dmap; (1S)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; 1: Esterification / 2: Esterification;

DOI:10.1021/ol0062704

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Tris-(2-tert-butoxycarbonylamino-acetoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid benzyl ester (302784-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / 10-camphorsulfonic acid / 16 h / 20 °C / vacuum

2: 68 percent / DCC; DMAP / CH₂Cl₂ / 16 h

With dmap; (1S)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; 1: Esterification / 2: Esterification;

DOI:10.1021/ol0062704

upstream raw materials:

BOC-glycine

benzyl 3α,7α,12α-trihydroxyl-5β-cholestane-24-carboxylic ester

cholic acid

benzyl alcohol