Benzyl (20beta)-3beta-hydroxy-12-oxoolean-12-en-29-oate

Base Information

• Chemical Name: Benzyl (20beta)-3beta-hydroxy-12-oxoolean-12-en-29-oate
• CAS No.: 51984-75-9
• Molecular Formula: C37H52O4
• Molecular Weight: 560.817
• European Community (EC) Number: 257-576-3
• DSSTox Substance ID: DTXSID30966302
• Nikkaji Number: J279.408J
• Wikidata: Q82948705
• ChEMBL ID: CHEMBL1269516
• Mol file: 51984-75-9.mol

Synonyms:51984-75-9;CHEMBL1269516;SCHEMBL20852131;Benzyl (20beta)-3beta-hydroxy-12-oxoolean-12-en-29-oate;DTXSID30966302;EINECS 257-576-3;AKOS016036163;Benzyl 3-hydroxy-11-oxoolean-12-en-29-oate;3beta-Hydroxy-11-oxooleana-12-ene-30-oic acid benzyl ester

Chemical Property of Benzyl (20beta)-3beta-hydroxy-12-oxoolean-12-en-29-oate

Chemical Property:

• PSA: 63.60000
• LogP: 8.07140
• XLogP3: 8.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 560.38656014
• Heavy Atom Count: 41
• Complexity: 1120

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)OCC6=CC=CC=C6)C)C)C)C
• Isomeric SMILES: C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)(C)C(=O)OCC6=CC=CC=C6

Technology Process of Benzyl (20beta)-3beta-hydroxy-12-oxoolean-12-en-29-oate

There total 7 articles about Benzyl (20beta)-3beta-hydroxy-12-oxoolean-12-en-29-oate 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%

enoxolone (471-53-4) + O-benzyl-N,N'-dicyclohexylisourea (6738-17-6) → benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate (51984-75-9)

Guidance literature:

In chloroform; for 5h; Heating;

DOI:10.1248/cpb.38.221

Reference yield: 94.0%

enoxolone (471-53-4) + benzyl chloride (100-44-7) → benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate (51984-75-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 3h;

DOI:10.1016/j.bmcl.2012.02.032

Reference yield: 92.6%

enoxolone (471-53-4) + benzyl bromide (100-39-0) → benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate (51984-75-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2012.03.081

upstream raw materials:

enoxolone

O-benzyl-N,N'-dicyclohexylisourea

6',6'',30-tribenzyl-18β-glycyrrhizin

benzyl bromide

Downstream raw materials:

benzyl 3-O-(methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate))-18β-glycyrrhetinate

benzyl (3β)-3-([N-(3-aminopropyl)glycyl]oxy)-11-oxo-olean-12-en-30-oate

Refernces

• 1、 Liang, Shuobin,Li, Man,Yu, Xiaojuan,Jin, Hongwei,Zhang, Yongmin,Zhang, Lihe,Zhou, Demin,Xiao, Sulong. "Synthesis and structure-activity relationship studies of water-soluble β-cyclodextrin-glycyrrhetinic acid conjugates as potential anti-influenza virus agents". . p. 328 - 338. Retrieved 2019.
• 2、 Zhou, Fei,Wu, Gao-Rong,Cai, De-Sheng,Xu, Bing,Yan, Meng-Meng,Ma, Tao,Guo, Wen-Bo,Zhang, Wen-Xi,Huang, Xue-Mei,Jia, Xiao-hui,Yang, Yu-Qin,Gao, Feng,Wang, Peng-Long,Lei, Hai-Min. "Synthesis and biological activity of glycyrrhetinic acid derivatives as antitumor agents". . p. 623 - 635. Retrieved 2019/06/21.