10246-36-3

Usage

Chemical classification

Belongs to the oleanane triterpenoids group.

Natural occurrence

Found in various plants.

Pharmacological properties

Exhibits anti-inflammatory, antioxidant, and cytotoxic activities.

Cancer treatment potential

Shown to have inhibitory effects on the growth of certain cancer cells.

Neuroprotective agent

Investigated for its potential as a neuroprotective agent.

Immune response modulation

Studied for its ability to modulate immune responses.

Medical applications

Shows promising potential for various medical applications.

Ongoing research

Continues to be the subject of scientific research.

Upstream product

• 100-51-6 benzyl alcohol 
• 67-56-1 methanol 
• 27570-20-3 betulin monoacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Relevant academic research and scientific papers

Sugar migration induced by the Wagner-Meerwein rearrangement of 28-O-glycosyl-betulin derivatives

Treatment of betulin-type saponins, in which the sugar moiety is connected at the 28-position, with TMSOTf affords 3-O-substituted allobetulin saponins. This unprecedented migration of the sugar part is driven by the Wagner-Meerwein rearrangement of the betulin core. According to our mechanistic studies an oxocarbenium ion released during the rearrangement reacts with the free 3-OH group of the triterpene affording the final allobetulin saponin. Migration rate depends on the size and configuration of the sugar moiety.

GLYCOSYLATION OF TRITERPENE ALCOHOLS OF THE LUPANE SERIES

The glycosylation of lupeol, allobetulin, 3β-28-dihydroxy-18-lupene, 3β-28-dihydroxy-18β,19β-epoxylupane and of betulin monoacetates in acetonitrile with mercury cyanide has ben studied.The 3- and 28-mono- and the 3,28-di-O-β-D-glucopyranosides of 3β-28-dihydroxy-18-lupene and of 3β-28-dihydroxy-18β,19β-epoxylupane have been synthesized for the first time.Preparative methods for the synthesis of glucosides of lupeol, of allobetulin, and of betulin 3- and 28-monoacetates are proposed.

GLYCOSYLATION OF BETULIN AND ITS ACETATES IN THE PRESENCE OF CADMIUM CARBONATE

The glycosylation of betulin and its acetates by α-acetobromoglucose in toluene in the presence of cadmium carbonate is considered.It has been shown that the reaction is accompanied by Wagner-Meerwein rearrangements of the initial alcohols in rings A and E.This leads to the formation - in addition to acetates of betulin glycosides - of derivatives of allobetulin - A-nor-Δ3(5)-allobetulin and A-nor-Δ3(5)-betulin - as was shown by 1H and 13C NMR spectroscopy.