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

Base Information

• Chemical Name: 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
• CAS No.: 1025965-86-9
• Molecular Formula: C₃₀H₄₂O₅
• Molecular Weight: 482.66
• Mol file: 1025965-86-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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:

24-(benzoyloxy)-chol-4-en-3-one (473462-28-1) → 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)

Guidance literature:

24-(benzoyloxy)-chol-4-en-3-one; With ozone; acetic acid; In ethyl acetate; at -20 - -10 ℃;

With dihydrogen peroxide; acetic acid; In water; ethyl acetate; at 20 ℃; Further stages.;

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) → 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)

Guidance literature:

Multi-step reaction with 8 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

With sodium tetrahydroborate; jones reagent; bromine; 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-4-cholenolate (1452-33-1) → 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)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 10percent NaOH / ethanol / 1.5 h / 20 °C

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

3.1: 72 percent / sodium borohydride / tetrahydrofuran; H₂O / 0 °C

4.1: 92 percent / triethylamine / tetrahydrofuran

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

5.2: 30percent hydrogen peroxide; acetic acid / ethyl acetate; H₂O / 20 °C

With sodium tetrahydroborate; ozone; acetic acid; triethylamine; In tetrahydrofuran; ethanol; water; ethyl acetate;

DOI:10.1021/jo0259109

upstream raw materials:

24-(benzoyloxy)-chol-4-en-3-one

Lithocholic acid

methyl lithocholate

methyl 3-oxo-5β-cholan-24-oate

Downstream raw materials:

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

Refernces