Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Base Information

• Chemical Name: Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester
• CAS No.: 161882-44-6
• Molecular Formula: C₄₂H₅₄O₈
• Molecular Weight: 686.886
• Mol file: 161882-44-6.mol

Synonyms:Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Chemical Property of Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

There total 5 articles about Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl 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: 83.0%

methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate (58822-33-6) + 4-biphenyl-carboxylic acid chloride (14002-51-8) → Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester (161882-44-6)

Guidance literature:

With calcium hydride; tetra-(n-butyl)ammonium iodide; In toluene; Heating;

DOI:10.1021/jo00107a015

Reference yield:

methyl 3α,12α-dihydroxy-7-oxo-5β-cholate (15073-97-9,15180-34-4,81644-39-5,81644-40-8,10538-65-5) → Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester (161882-44-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / DMAP, Et₃N / 24 h / Ambient temperature

2: 83 percent / NaBH₄ / methanol / 1 h / 0 °C

3: 83 percent / CaH₂, n-Bu₄NI / toluene / Heating

With dmap; sodium tetrahydroborate; calcium hydride; tetra-(n-butyl)ammonium iodide; triethylamine; In methanol; toluene;

DOI:10.1021/jo00107a015

Reference yield:

methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate) (21066-20-6) → Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetoxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester (161882-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / NaBH₄ / methanol / 1 h / 0 °C

2: 83 percent / CaH₂, n-Bu₄NI / toluene / Heating

With sodium tetrahydroborate; calcium hydride; tetra-(n-butyl)ammonium iodide; In methanol; toluene;

DOI:10.1021/jo00107a015

upstream raw materials:

methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate

4-biphenyl-carboxylic acid chloride

methyl 3α,12α-dihydroxy-7-oxo-5β-cholate

methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate)

Downstream raw materials:

Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-3-hydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester

Biphenyl-4-carboxylic acid (3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-12-acetoxy-3-acryloyloxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-7-yl ester