(2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester

Base Information

• Chemical Name: (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester
• CAS No.: 876723-81-8
• Molecular Formula: C37H52 O4
• Molecular Weight: 560.817
• Mol file: 876723-81-8.mol

Synonyms:(2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester;(2alpha)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester

Chemical Property of (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester

Chemical Property:

• PSA: 63.60000
• LogP: 8.07140

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl ester

There total 6 articles about (2α)-2-Hydroxy-3-oxo-olean-12-en-28-oic acid phenylmethyl 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: 80.0%

(4aS,6aS,6bR,12aR)-benzyl 2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate (869788-74-9) → 2α-hydroxy-3-oxoolean-12-en-28-oic acid benzyl ester (876723-81-8)

Guidance literature:

With sulfuric acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; at 0 ℃;

DOI:10.1016/j.bmcl.2005.10.014

Reference yield:

Oleanolic acid (508-02-1) → 2α-hydroxy-3-oxoolean-12-en-28-oic acid benzyl ester (876723-81-8)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide / 50 °C

2: PCC / CH₂Cl₂

3: 80 percent / mCPBA; H₂SO₄ / methanol; CH₂Cl₂ / 0 °C

With sulfuric acid; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.10.014

Reference yield:

oleanolic acid benzyl ester (303114-51-4) → 2α-hydroxy-3-oxoolean-12-en-28-oic acid benzyl ester (876723-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: PCC / CH₂Cl₂

2: 80 percent / mCPBA; H₂SO₄ / methanol; CH₂Cl₂ / 0 °C

With sulfuric acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.10.014

upstream raw materials:

(4aS,6aS,6bR,12aR)-benzyl 2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Oleanolic acid

benzyl chloride

oleanolic acid benzyl ester

Downstream raw materials:

2α-methoxymethyloxy-3-oxoolean-12-en-28-oic acid benzyl ester

C₄₄H₅₈O₄

2α-methoxymethyloxy-3β-hydroxy-olean-12-en-28-oic acid benzyl ester

C₄₄H₆₀O₄

Refernces

• 1、 Qian, Shan,Li, Haijiao,Chen, Yin,Zhang, Weiyu,Yang, Shengyong,Wu, Yong. "Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B". scheme or table. p. 1743 - 1750. Retrieved 2011/03/18.
• 2、 Wen, Xiaoan,Sun, Hongbin,Liu, Jun,Cheng, Keguang,Zhang, Pu,Zhang, Liying,Hao, Jia,Zhang, Luyong,Ni, Peizhou,Zographos, Spyros E.,Leonidas, Demettes D.,Alexacou, Kyra-Melinda,Gimisis, Thanasis,Hayes, Joseph M.,Oikonomakos, Nikos G.. "Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: Synthesis, structure-activity relationships, and X-ray crystallographic studies". experimental part. p. 3540 - 3554. Retrieved 2009/04/07.