(3α,5β,6α)-6-ethyl-3-hydroxy-7-oxo-cholan-24-oic acid methyl ester (BTC-C1)

Base Information

• Chemical Name: (3α,5β,6α)-6-ethyl-3-hydroxy-7-oxo-cholan-24-oic acid methyl ester (BTC-C1)
• CAS No.: 462122-38-9
• Molecular Formula: C27H44O4
• Molecular Weight: 432.644
• Mol file: 462122-38-9.mol

Synonyms:(3α,5β,6α)-6-ethyl-3-hydroxy-7-oxo-cholan-24-oic acid methyl ester (BTC-C1);OCA-J

Chemical Property of (3α,5β,6α)-6-ethyl-3-hydroxy-7-oxo-cholan-24-oic acid methyl ester (BTC-C1)

Chemical Property:

• Boiling Point: 524.5±25.0 °C(Predicted)
• PKA: 15.03±0.70(Predicted)
• PSA: 63.60000
• Density: 1.054±0.06 g/cm3(Predicted)
• LogP: 5.41060

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3α,5β,6α)-6-ethyl-3-hydroxy-7-oxo-cholan-24-oic acid methyl ester (BTC-C1)

There total 2 articles about (3α,5β,6α)-6-ethyl-3-hydroxy-7-oxo-cholan-24-oic acid methyl ester (BTC-C1) 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: 100.0%

3α-hydroxy-6-ethylidene-7-keto-5β-cholan-24-carboxylic acid methyl ester (863239-59-2,1516887-31-2) → 3α-hydroxy-6α-ethyl-7-keto-5β-cholanic acid methyl ester (462122-38-9)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/jm401873d

Reference yield:

3α-hydroxy-6-ethylidene-7-keto-5β-cholan-24-carboxylic acid methyl ester (863239-59-2,1516887-31-2) → 3α-hydroxy-6β-ethyl-7-keto-5β-cholanic acid methyl ester + 3α-hydroxy-6α-ethyl-7-keto-5β-cholanic acid methyl ester (462122-38-9)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; water; at 40 ℃; under 2280.15 Torr; Temperature; Pressure; Reagent/catalyst; Overall yield = 97.8 %; Overall yield = 29.5 g; stereoselective reaction;

Reference yield:

3α-hydroxy-6α-ethyl-7-keto-5β-cholanic acid methyl ester (462122-38-9) → 23-N-(carbocinnamyloxy)-3α,7α-diformyloxy-6α-ethyl-24-nor-5β-cholan-23-amine

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydroxide / methanol

2: sodium tetrahydroborate; water / tetrahydrofuran / 20 °C

3: toluene-4-sulfonic acid / benzene / 2 h / Reflux

4: oxalyl dichloride / 2 h / 45 °C / Inert atmosphere

5: sodium azide / water; acetone / 3 h / 0 - 5 °C

6: toluene / 5 h / Reflux

7: toluene / Inert atmosphere; Reflux

With sodium tetrahydroborate; sodium azide; oxalyl dichloride; water; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; methanol; water; acetone; toluene; benzene; 6: Curtius rearrangement;

DOI:10.1016/j.bmc.2011.03.004

upstream raw materials:

3α-hydroxy-6-ethylidene-7-keto-5β-cholan-24-carboxylic acid methyl ester

Downstream raw materials:

6α-ethyl-3α-formyloxy-7-keto-5β-cholan-24-oic acid

6β-ethyl-3α,7β-dihydroxy-5β-cholan-24-ol

6β-ethyl-3α,7α-dihydroxy-5β-cholan-24-ol