11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester

Base Information

• Chemical Name: 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester
• CAS No.: 173106-33-7
• Molecular Formula: C₅₀H₇₆FNO₅S
• Molecular Weight: 822.222
• Mol file: 173106-33-7.mol

Synonyms:11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester

Chemical Property of 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester

There total 4 articles about 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl 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: 66.0%

4-Fluorothiophenol (371-42-6) + 11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-(1-bromomethyl-vinyl)-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid methyl ester (173106-29-1) → 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester (173106-33-7)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; for 144h; Heating;

DOI:10.1021/jm950670t

Reference yield:

3-O-acetylbetulinic acid (10376-50-8,38736-81-1) → 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester (173106-33-7)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl chloride / CHCl₃ / 18 h / Ambient temperature

2: 98.6 percent / triethylamine / CH₂Cl₂ / 16 h

3: 100 percent / N-bromosuccinimide / CCl₄ / 72 h / Ambient temperature

4: 66 percent / palladium acetate, triphenylphosphine, triethylamine / tetrahydrofuran / 144 h / Heating

With N-Bromosuccinimide; oxalyl dichloride; palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; dichloromethane; chloroform;

DOI:10.1021/jm950670t

Reference yield:

3-O-acetylbetulinic acid chloride (59868-82-5) → 11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-[1-(4-fluoro-phenylsulfanylmethyl)-vinyl]-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid methyl ester (173106-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98.6 percent / triethylamine / CH₂Cl₂ / 16 h

2: 100 percent / N-bromosuccinimide / CCl₄ / 72 h / Ambient temperature

3: 66 percent / palladium acetate, triphenylphosphine, triethylamine / tetrahydrofuran / 144 h / Heating

With N-Bromosuccinimide; palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; dichloromethane;

DOI:10.1021/jm950670t

upstream raw materials:

4-Fluorothiophenol

11-{[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-Acetoxy-1-(1-bromomethyl-vinyl)-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl]-amino}-undecanoic acid methyl ester

3-O-acetylbetulinic acid

3-O-acetylbetulinic acid chloride

Downstream raw materials:

11-({(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-[1-(4-Fluoro-phenylsulfanylmethyl)-vinyl]-9-hydroxy-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carbonyl}-amino)-undecanoic acid