3-Epimaslinic acid benzyl ester

Base Information

• Chemical Name: 3-Epimaslinic acid benzyl ester
• CAS No.: 876723-86-3
• Molecular Formula: C37H54 O4
• Molecular Weight: 562.833
• Mol file: 876723-86-3.mol

Synonyms:3-Epimaslinic acid benzyl ester;(2alpha,3alpha)-2,3-Dihydroxy-olean-12-en-28-oic acid phenylmethyl ester

Chemical Property of 3-Epimaslinic acid benzyl ester

Chemical Property:

• PSA: 66.76000
• LogP: 7.86320

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Epimaslinic acid benzyl ester

There total 6 articles about 3-Epimaslinic acid benzyl 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: 77.0%

2α-hydroxy-3-oxoolean-12-en-28-oic acid benzyl ester (876723-81-8) → benzyl-2α,3α-dihydroxyolean-12-en-28-oic acid (876723-86-3) + benzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate (464876-77-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.bmcl.2005.10.014

Reference yield:

(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) → benzyl-2α,3α-dihydroxyolean-12-en-28-oic acid (876723-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / mCPBA; H₂SO₄ / methanol; CH₂Cl₂ / 0 °C

2: 18 percent / NaBH₄ / tetrahydrofuran / 0 °C

With sodium tetrahydroborate; sulfuric acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2005.10.014

Reference yield:

Oleanolic acid (508-02-1) → benzyl-2α,3α-dihydroxyolean-12-en-28-oic acid (876723-86-3)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / dimethylformamide / 50 °C

2: PCC / CH₂Cl₂

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

4: 18 percent / NaBH₄ / tetrahydrofuran / 0 °C

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

DOI:10.1016/j.bmcl.2005.10.014

upstream raw materials:

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

(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

Refernces

• 1、 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.