(2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester,

Base Information

• Chemical Name: (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester,
• CAS No.: 876724-09-3
• Molecular Formula: C₃₂H₅₂O₅
• Molecular Weight: 516.762
• Mol file: 876724-09-3.mol

Synonyms:(2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester,;(2alpha,3beta)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester

Chemical Property of (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester,

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl ester,

There total 8 articles about (2α,3β)-2,3-Dihydroxy-olean-12-en-28-oic acid 2-hydroxyethyl 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: 84.0%

maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4) + 2-bromoethanol (540-51-2) → 2-hydroxyethyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate (876724-09-3)

Guidance literature:

maslinic acid; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

2-bromoethanol; In N,N-dimethyl-formamide; for 18h;

DOI:10.1016/j.ejmech.2013.10.016

Reference yield: 78.0%

28-(2-bromoethyl)maslinic acid ester (876724-03-7) → 2-hydroxyethyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate (876724-09-3)

Guidance literature:

With ethanol; triethylamine; Heating;

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) → 2-hydroxyethyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate (876724-09-3)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 77 percent / NaBH₄ / tetrahydrofuran / 0 °C

3: 100 percent / H₂ / Pd/C / tetrahydrofuran / 20 °C

4: K₂CO₃ / dimethylformamide / 20 °C

5: 78 percent / aq. ethanol; Et₃N / Heating

With sodium tetrahydroborate; ethanol; sulfuric acid; hydrogen; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2005.10.014

upstream raw materials:

28-(2-bromoethyl)maslinic acid 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

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

Oleanolic acid

Refernces

• 1、 Siewert, Bianka,Pianowski, Elke,Csuk, René. "Esters and amides of maslinic acid trigger apoptosis in human tumor cells and alter their mode of action with respect to the substitution pattern at C-28". . p. 259 - 272. Retrieved 2013/11/19.