676530-80-6

Upstream product

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

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 academic research and scientific papers

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.

Synthesis and Evaluation of a Series of Oleanolic Acid Saponins as α-Glucosidase and α-Amylase Inhibitors

Sixteen naturally occurring oleanolic acid saponins and their derivatives were synthesized in an efficient and practical strategy, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. Among all the compounds, 28-O-m

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

Glycoside modification of oleanolic acid derivatives as a novel class of anti-osteoclast formation agents

Oleanolic acid, a natural product, possesses an anti-osteoclast formation activity. Targeting at discovery of novel and potent anti-bone resorption agents, 22 glycosides of oleanolic acid derivatives (including d-galactopyranosides, d-glucopyranosides, d-xylopyranoses, d-arabopyranoses and d-glycuronic acids) were synthesized at phase-transfer-catalyzed conditions (K2CO3, Bu4NBr, CH2Cl2-H2O) and their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) induced by 1α, 25-dihydroxy vitamin D3 was evaluated in a co-culture assay system. The structure-activity relationships of these compounds were also discussed.

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.

Facile Synthesis of Ginsenoside Ro

Two concise synthetic routes, being different in the glycosylation sequence, toward ginsenoside Ro (1) are developed. These syntheses feature the elaboration of the glucuronide residue at a later stage via the TEMPO-mediated selective oxidation and the installation of AZMB as a benzoylic neighboring participating group capable of being selectively removed afterward.

Synthesis of a typical glucuronide-containing saponin, 28-O-β-D- glucopyranosyl oleanate 3-O-β-D-galactopyranosyl-(1→2)-[β-D- glucopyranosyl-(1→3)]-β-D-glucuronopyranoside

28-O-β-D-Glucopyranosyl oleanate 3-O-β-D-galactopyranosyl- (1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucuronopyranoside (1), a structurally typical glucuronide-containing triterpene saponin isolated from Aralia dasyphylla, was concisely synthesized in linear nine steps and 26% overall yield. The key features of the synthesis are: (1) attachment of the 28-glucosyl ester ahead of assembly of the 3-O-sugar chain; (2) elaboration of the glucuronide residue at a later stage via the TEMPO-mediated selective oxidation; (3) installation of 2-(azidomethyl)benzoyl group as a benzoylic neighboring participating group which is selectively removed afterwards for synthesis of the 1→2 sugar linkage.