Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester

Base Information

• Chemical Name: Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester
• CAS No.: 95826-32-7
• Molecular Formula: C₂₉H₃₆O₅
• Molecular Weight: 464.602
• Mol file: 95826-32-7.mol

Synonyms:

Chemical Property of Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester

There total 7 articles about Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-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: 57.0%

Isopropenyl acetate (108-22-5) + Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-6a,11b-dimethyl-2-oxo-hexadecahydro-5-oxa-cyclopenta[a]pyren-7-yl ester (95826-30-5) → Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-3H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester (95826-31-6) + Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester (95826-32-7)

Guidance literature:

toluene-4-sulfonic acid; Yields of byproduct given;

DOI:10.1016/S0040-4039(01)91242-0

Reference yield:

androsta-1,4-diene-3,11,17-trione (7738-93-4) → Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester (95826-32-7)

Guidance literature:

Multi-step reaction with 7 steps

2: 85 percent / glacial AcOH, 48percent aq.HBr / 0.5 h

3: 80 percent / ZnBr₂ / CH₂Cl₂ / 25 °C

4: 1.) triethylsilane, trifluoroacetic acid; 2.) KOH / 1.) CH₂Cl₂, 50 deg C, 20 h; 2.) MeOH, THF, 25 deg C

5: 92 percent

6: 76 percent / deprotection

7: p-TsOH

With triethylsilane; potassium hydroxide; hydrogen bromide; acetic acid; trifluoroacetic acid; zinc dibromide; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(01)91242-0

Reference yield:

(3aS,6aS,9aS,9bS,11bS)-6a,11b-Dimethyl-3a,6,6a,8,9,9a,9b,10,11,11b-decahydro-3H,4H-5-oxa-cyclopenta[a]pyrene-2,7-dione (95826-24-7) → Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-2-acetoxy-6a,11b-dimethyl-3a,5a,6,6a,7,8,9,9a,9b,10,11,11a,11b,11c-tetradecahydro-1H,4H-5-oxa-cyclopenta[a]pyren-7-yl ester (95826-32-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / ZnBr₂ / CH₂Cl₂ / 25 °C

2: 1.) triethylsilane, trifluoroacetic acid; 2.) KOH / 1.) CH₂Cl₂, 50 deg C, 20 h; 2.) MeOH, THF, 25 deg C

3: 92 percent

4: 76 percent / deprotection

5: p-TsOH

With triethylsilane; potassium hydroxide; trifluoroacetic acid; zinc dibromide; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(01)91242-0

upstream raw materials:

Isopropenyl acetate

Benzoic acid (3aS,5aR,6aS,9aS,9bS,11aR,11bR,11cS)-6a,11b-dimethyl-2-oxo-hexadecahydro-5-oxa-cyclopenta[a]pyren-7-yl ester

androsta-1,4-diene-3,11,17-trione

C₂₂H₃₄O₂S₂