oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester

Base Information

• Chemical Name: oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester
• CAS No.: 676530-80-6
• Molecular Formula: C₆₄H₇₄O₁₂
• Molecular Weight: 1035.28
• Mol file: 676530-80-6.mol

Synonyms:oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester

Chemical Property of oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester

There total 3 articles about oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl 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: 95.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1221151-98-9) + Oleanolic acid (508-02-1) → oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester (676530-80-6)

Guidance literature:

With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; chemoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.01.039

Reference yield: 90.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + Oleanolic acid (508-02-1) → oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester (676530-80-6)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In dichloromethane; Heating;

DOI:10.1055/s-2003-44985

Reference yield: 63.0%

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate (1221151-98-9) + Oleanolic acid (508-02-1) → C98H100O21 (1221152-08-4) + oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester (676530-80-6)

Guidance literature:

With trifluoromethanesulfonyloxy(triphenylphosphine)gold(I); boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; chemoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.01.039

upstream raw materials:

2,3,4,6-tetra-O-benzoylglucosyl bromide

Oleanolic acid

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate

Downstream raw materials:

28-O-β-D-glucopyranosyl oleanolate

28-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oleanate 3-O-(2,4-di-O-benzoyl-3-O-benzyl-6-O-trityl-β-D-glucopyranoside)

Refernces

• 1、 Guo, Tiantian,Wu, Shaoping,Guo, Sen,Bai, Lu,Liu, Qingchao,Bai, Naisheng. "Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α-Glucosidase and α-Amylase Inhibitors". . p. 615 - 628. Retrieved 2015/09/15.
• 2、 Li, Jun-Feng,Chen, Song-Jie,Zhao, Yu,Li, Jian-Xin. "Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents". experimental part. p. 599 - 605. Retrieved 2009/05/27.