(4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate

Base Information

• Chemical Name: (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate
• CAS No.: 65023-19-0
• Molecular Formula: C31H48O4
• Molecular Weight: 484.72
• Mol file: 65023-19-0.mol

Synonyms:Methyl (3α,5ξ,18α)-3-hydroxy-12-oxoolean-9(11)-en-28-oate;Olean-9(11)-en-28-oic acid, 3-hydroxy-12-oxo-, methyl ester, (3β)-;(4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate;Methyl (4aS,6aR,6bS,8aR,10S,12aS,14aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-14-oxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydropicene-4a(2H)-carboxylate

Chemical Property of (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate

Chemical Property:

• PSA: 63.60000
• LogP: 6.50100

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate

There total 10 articles about (4aS,6aR,6bS,10R,12aS,14aR,14bR)-Methyl 10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate 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: 99.0%

methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate (65023-20-3) → methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate (65023-19-0)

Guidance literature:

With potassium hydroxide; In methanol; for 1h; Reflux;

DOI:10.1021/acs.jmedchem.5b01292

Reference yield:

oleanolic acid methyl ester (1724-17-0,73584-64-2) → methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate (65023-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: 30percent H₂O₂ / acetic acid

3: Br₂, HBr / acetic acid

4: KOH / methanol

With potassium hydroxide; hydrogen bromide; dihydrogen peroxide; bromine; In pyridine; methanol; acetic acid;

DOI:10.1016/S0960-894X(97)00279-5

Reference yield:

Oleanolic acid (508-02-1) → methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate (65023-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2.2: 24 h / 35 °C / Inert atmosphere

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol400399x

upstream raw materials:

3β-hydroxy-12-oxoolean-9(11)-en-28-oic acid

methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate

methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate

oleanolic acid methyl ester

Downstream raw materials:

1,2-dihydro-2-cyano-3,12-dioxooleana-1,9⁽¹¹⁾-dien-28-oic acid methyl ester

methyl 2-hydroxymethylene-3,12-dioxoolean-9⁽¹¹⁾-en-28-oate

bardoxolone methyl

bardoxolone