Corosolic acid benzyl ester

Base Information

• Chemical Name: Corosolic acid benzyl ester
• CAS No.: 869788-73-8
• Molecular Formula: C37H54 O4
• Molecular Weight: 562.833
• Mol file: 869788-73-8.mol

Synonyms:(2alpha,3beta)-2,3-Dihydroxy-urs-12-en-28-oic acid phenylmethyl ester

Chemical Property of Corosolic acid benzyl ester

Chemical Property:

• PSA: 66.76000
• LogP: 7.71910

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Corosolic acid benzyl ester

There total 8 articles about Corosolic 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: 68.0%

benzyl-2α-hydroxy-3-oxours-12-en-28-oic acid (958237-69-9) → benzyl-2α,3β-dihydroxyurs-12-en-28-oic acid (869788-73-8) + benzyl-2α,3α-dihydroxyurs-12-en-28-oic acid

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1016/j.bmcl.2007.08.057

Reference yield: 55.0%

(1S,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-10-Acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester (869788-72-7) → benzyl-2α,3β-dihydroxyurs-12-en-28-oic acid (869788-73-8)

Guidance literature:

(1S,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-10-Acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester; With borane-THF;

With sodium hydroxide; dihydrogen peroxide;

DOI:10.1016/j.bmcl.2005.08.026

Reference yield:

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate (192211-41-9) → benzyl-2α,3β-dihydroxyurs-12-en-28-oic acid (869788-73-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 89 percent / PCC / CH₂Cl₂ / 24 h / 0 °C

2.1: 91 percent / H₂SO₄ / 100 °C

3.1: BH₃*THF

3.2: 55 percent / aq. NaOH; H₂O₂

With borane-THF; sulfuric acid; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/j.bmcl.2005.08.026

upstream raw materials:

(1S,2R,4aS,6aS,6bR,8aR,12aR,12bR,14bS)-10-Acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester

benzyl-2α-hydroxy-3-oxours-12-en-28-oic acid

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

benzyl (1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,-11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate

Downstream raw materials:

corosolic acid

Refernces

• 1、 Nelson, Andrew T.,Camelio, Andrew M.,Claussen, Karin R.,Cho, Jiyoon,Tremmel, Lisa,Digiovanni, John,Siegel, Dionicio. "Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties". . p. 4342 - 4346. Retrieved 2015/11/03.
• 2、 Wen, Xiaoan,Xia, Jun,Cheng, Keguang,Zhang, Liying,Zhang, Pu,Liu, Jun,Zhang, Luyong,Ni, Peizhou,Sun, Hongbin. "Pentacyclic triterpenes. Part 5: Synthesis and SAR study of corosolic acid derivatives as inhibitors of glycogen phosphorylases". . p. 5777 - 5782. Retrieved 2008/04/03.