676530-80-6

Basic information

• Product Name: oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester
• Synonyms: oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester
• CAS NO: 676530-80-6
• Molecular Weight: 1035.28
• Mol File: 676530-80-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester(676530-80-6)
• EPA Substance Registry System: oleanolic acid 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl ester(676530-80-6)

Safety Data

• Hazardous Substances Data: 676530-80-6(Hazardous Substances Data)

Upstream product

• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 
• 508-02-1 Oleanolic acid 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 

Downstream Products

• 1039373-70-0 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) 
• 14162-53-9 28-O-β-D-glucopyranosyl oleanolate 

Relevant articles and documents

Stereocontrolled synthesis of oleanolic saponin ladyginoside A isolated from Ladyginia bucharica

Efficient stereocontrolled synthesis of ladyginoside A isolated from Ladyginia bucharica is described. The presented methodology bases on the β-selective glycosylation to construct oleanate-3-O-β-glycoside from selectively protected D-cellobiose comprising desired β-linkage in carbohydrate unit. By using this procedure, dimethyl ester of ladyginoside A (1) (methyl oleanate 3-O-(β-D-glucopyranosyl)-(1 → 4)-β-D-glucuronide methyl ester) was obtained in 16% overall yield. Elaborated synthesis is also demonstrated as useful methodology en route to saponin 2 with additional glucose unit, namely 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucuronide] oleanolic acid 28-O-β-D-glucopyranosyl ester.

Chemoselective glycosylation of carboxylic acid with glycosyl ortho-hexynylbenzoates as donors

The gold(I)-catalyzed glycosylation of acid alcohols with glycosyl ortho-hexynylbenzoates in the presence of BF3·Et2O and DBU provided the corresponding ester glycosides chemoselectively in high yield; while with DTBP as an additive

Synthesis of betavulgaroside III, a representative triterpene seco-glycoside

(Chemical Equation Presented) Triterpene seco-glycosides constitute a small family of the plant saponins which feature a terminal seco-saccharide appendage deriving supposedly from oxidative scission of a monosaccharide unit. Herein, we have developed synthetic approaches for the first time to the access to these molecules. Betavulgaroside III (1), a representative congener occurring in Beta vulgaris and Achyranthes fauriei, is successfully synthesized in a total of 31 steps with L-arabinose, D-glucose, and oleanolic acid as starting materials. The longest linear sequence requires 23 steps and in an overall 0.9% yield (from D-glucose). The synthesis features oxidative elaboration of the seco-saccharide unit prior to assembly of the triterpene 3,28-bisglycoside. This tactic has been proven superior, in the attempts to the synthesis of the more easily accessible 2″-epi-betavulgaroside III (2), to that employing oxidative cleavage of the terminal saccharide unit at an advanced triterpene 3,28-bisglycoside scaffold.