65615-69-2

Usage

Uses

Used in Pharmaceutical Industry:
.beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate is used as an intermediate in the synthesis of heparin building blocks for the development of heparin-based drugs. Heparin is a highly sulfated glycosaminoglycan that plays a crucial role in various biological processes, including blood clotting and wound healing. It is widely used as an anticoagulant in the treatment and prevention of thromboembolic disorders.
In the pharmaceutical industry, .beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate serves as a vital component in the production of heparin, which is an essential drug for managing various medical conditions related to blood clotting. The synthesis of heparin building blocks using .beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate allows for the development of more effective and targeted heparin-based therapies, ultimately benefiting patients with clotting disorders and other related health issues.

Upstream product

• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 108032-41-3 methyl 1,2,3,4-tetra-O-acetyl-α-L-idopyranuronate 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 75860-76-3 methyl 1,2,3-tri-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranuronate 
• 30902-96-6 methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Relevant academic research and scientific papers

The stereoselectivities of tributyltin hydride-mediated reductions of 5-bromo-d-glucuronides to l-iduronides are dependent on the anomeric substituent: Syntheses and DFT calculations

One of the shortest synthetic routes to l-iduronic acid derivatives is via free radical reduction of the C-5 bromide of the corresponding protected d-glucuronic acid derivative. The epimerization of such C-5 bromides to the l-ido derivatives via reaction with tributyltin hydride was investigated. It was found that the stereoselectivity of the reaction was dependent on the anomeric substituent. If the substituent was fluoride the l-ido product was obtained exclusively in 65-72% yield whereas the O-methyl or O-acetyl derivatives led to isomeric mixtures of both the l-ido and d-gluco products in different ratios depending on the reaction conditions. DFT calculations were performed to determine the stereoelectronic factors that favour formation of the l-ido isomer from the fluoride and suggest the selectivity is due to a transition state gauche effect and an Sn-F interaction.

Novel efficient routes to heparin monosaccharides and disaccharides achieved via regio- and stereoselective glycosidation

A new methodology for the synthesis of heparin building blocks has been developed. We describe novel efficient routes to both L-iduronic acid and D-glucuronic acid acceptors. Glycosylation with thioglycosides donors gave corresponding disaccharides in a regio- and stereoselective fashion. An improved approach to synthesizing azido-glucose thioglycoside donor to render azido-sugar from mannose via nucleophilic substitution is described.

Radical-mediated bromination of carbohydrate derivatives: Searching for alternative reaction conditions without carbon tetrachloride

KBrO3-Na2S2O4 in CH2Cl2-H2O or PhCF3-H2O biphasic solvent systems was applied to the bromination of several monosaccharide derivatives having capto-datively