24-(benzoyloxy)-4-oxachol-5-en-3-one

Base Information

• Chemical Name: 24-(benzoyloxy)-4-oxachol-5-en-3-one
• CAS No.: 473462-29-2
• Molecular Formula: C₃₀H₄₀O₄
• Molecular Weight: 464.645
• Mol file: 473462-29-2.mol

Synonyms:24-(benzoyloxy)-4-oxachol-5-en-3-one

Chemical Property of 24-(benzoyloxy)-4-oxachol-5-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 24-(benzoyloxy)-4-oxachol-5-en-3-one

There total 10 articles about 24-(benzoyloxy)-4-oxachol-5-en-3-one 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: 58.0%

Benzoic acid (R)-4-[(3R,3aR,5aS,6R,9aS,9bS)-6-(2-carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalen-3-yl]-pentyl ester (1025965-86-9) → 24-(benzoyloxy)-4-oxachol-5-en-3-one (473462-29-2)

Guidance literature:

With perchloric acid; acetic anhydride; In ethyl acetate;

DOI:10.1021/jo0259109

Reference yield:

methyl lithocholate (1249-75-8,5405-42-5,15074-01-8,15074-02-9,20231-51-0,63814-53-9,106757-10-2,125412-30-8) → 24-(benzoyloxy)-4-oxachol-5-en-3-one (473462-29-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 91 percent / Jones reagent / acetone / 0.17 h / 0 °C

2.1: bromine; acetic acid / 20 °C

3.1: 68 percent / Li₂CO₃; LiBr / dimethylformamide / 150 °C

4.1: 10percent NaOH / ethanol / 1.5 h / 20 °C

5.1: triethylamine / tetrahydrofuran / 1.5 h / 0 °C

6.1: 72 percent / sodium borohydride / tetrahydrofuran; H₂O / 0 °C

7.1: 92 percent / triethylamine / tetrahydrofuran

8.1: ozone; acetic acid / ethyl acetate / -20 - -10 °C

8.2: 30percent hydrogen peroxide; acetic acid / ethyl acetate; H₂O / 20 °C

9.1: 58 percent / acetic anhydride; perchloric acid / ethyl acetate

With sodium tetrahydroborate; perchloric acid; jones reagent; bromine; acetic anhydride; lithium carbonate; ozone; acetic acid; triethylamine; lithium bromide; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 1.1: Jones oxidation;

DOI:10.1021/jo0259109

Reference yield:

methyl 3-oxo-5β-cholan-24-oate (1173-32-6) → 24-(benzoyloxy)-4-oxachol-5-en-3-one (473462-29-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: bromine; acetic acid / 20 °C

2.1: 68 percent / Li₂CO₃; LiBr / dimethylformamide / 150 °C

3.1: 10percent NaOH / ethanol / 1.5 h / 20 °C

4.1: triethylamine / tetrahydrofuran / 1.5 h / 0 °C

5.1: 72 percent / sodium borohydride / tetrahydrofuran; H₂O / 0 °C

6.1: 92 percent / triethylamine / tetrahydrofuran

7.1: ozone; acetic acid / ethyl acetate / -20 - -10 °C

7.2: 30percent hydrogen peroxide; acetic acid / ethyl acetate; H₂O / 20 °C

8.1: 58 percent / acetic anhydride; perchloric acid / ethyl acetate

With sodium tetrahydroborate; perchloric acid; bromine; acetic anhydride; lithium carbonate; ozone; acetic acid; triethylamine; lithium bromide; In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo0259109

upstream raw materials:

Benzoic acid (R)-4-[(3R,3aR,5aS,6R,9aS,9bS)-6-(2-carboxy-ethyl)-3a,6-dimethyl-7-oxo-dodecahydro-cyclopenta[a]naphthalen-3-yl]-pentyl ester

Lithocholic acid

methyl lithocholate

methyl 3-oxo-5β-cholan-24-oate

Refernces