65615-69-2

Basic information

• Product Name: .beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate
• Synonyms: .beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate
• CAS NO: 65615-69-2
• Molecular Formula: C₁₅H₁₉BrO₁₁
• Molecular Weight: 455.21
• Mol File: 65615-69-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: .beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate(65615-69-2)
• EPA Substance Registry System: .beta.-D-Glucopyranuronic acid, 5-C-bromo-, methyl ester, tetraacetate(65615-69-2)

Safety Data

• Hazardous Substances Data: 65615-69-2(Hazardous Substances Data)

Usage

Uses

5-Bromo-β-D-glucopyranuronic Acid Methyl Ester Tetraacetate is an intermediate in the synthesis of heparin building blocks.

Upstream product

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

Downstream Products

• 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 
• 75860-76-3 methyl 1,2,3-tri-O-acetyl-4-deoxy-α-L-threo-hex-4-enopyranuronate 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 108032-41-3 methyl 1,2,3,4-tetra-O-acetyl-α-L-idopyranuronate 

Relevant articles and documents

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.

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