eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate

Base Information

• Chemical Name: eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate
• CAS No.: 452303-19-4
• Molecular Formula: C₆₀H₈₇F₆N₅O₆
• Molecular Weight: 1088.37
• Mol file: 452303-19-4.mol

Synonyms:eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate

Chemical Property of eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate

There total 7 articles about eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate 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: 80.0%

p-trifluoromethyl-phenylisocyanate (1548-13-6) + eicosyl 3α-azido-7α,12α-dihydroxy-5β-cholan-24-oate (452303-17-2) → eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate (452303-19-4)

Guidance literature:

With chloro-trimethyl-silane; In 1,2-dichloro-ethane; at 40 ℃; for 16h;

DOI:10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO;2-J

Reference yield:

1-Bromoeicosane (4276-49-7) + (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Azido-10,13-dimethyl-7,12-bis-(4-trifluoromethyl-phenylcarbamoyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid → eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate (452303-19-4)

Guidance literature:

(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Azido-10,13-dimethyl-7,12-bis-(4-trifluoromethyl-phenylcarbamoyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid; With caesium carbonate; In methanol;

1-Bromoeicosane; In N,N-dimethyl-formamide; at 47 ℃; for 24h; Further stages.;

DOI:10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO;2-H

Reference yield:

1-Bromoeicosane (4276-49-7) → eicosyl 3α-azido-7α,12α-di[(p-trifluoromethyl)phenylaminocarbonyloxy]-5β-cholan-24-oate (452303-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: aq. Cs₂CO₃ / methanol

1.2: 89 percent / NaI / dimethylformamide / 168000 h / 47 °C

2.1: 65 percent / Ph₃P; DEAD; Et₃N / tetrahydrofuran / 40 °C

3.1: 90 percent / NaN₃; N,N'-dimethyl-N,N'-propylene urea / 16 h / 40 °C

4.1: 80 percent / Me₃SiCl / 1,2-dichloro-ethane / 16 h / 40 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; chloro-trimethyl-silane; sodium azide; caesium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1,2-dichloro-ethane;

DOI:10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO;2-J

upstream raw materials:

1-Bromoeicosane

p-trifluoromethyl-phenylisocyanate

eicosyl 3α-azido-7α,12α-dihydroxy-5β-cholan-24-oate

cholic acid

Downstream raw materials:

(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-10,13-dimethyl-7,12-bis-(4-trifluoromethyl-phenylcarbamoyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester