262849-67-2

Basic information

• Product Name: 2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL CYANIDE
• Synonyms: 2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL CYANIDE;2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-SS-D-GLUCOPYRANOSYL CYANIDE;2-Bromo-2-deoxy-3,4,5,7-tetra-O-benzoyl-a-D-gluco-heptulopyranosononitrile
• CAS NO: 262849-67-2
• Molecular Formula: C35H27BrNO8
• Molecular Weight: 669.49478
• Mol File: 262849-67-2.mol

Chemical Properties

• Boiling Point: 772.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.50±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL CYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL CYANIDE(262849-67-2)
• EPA Substance Registry System: 2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL CYANIDE(262849-67-2)

Safety Data

• Hazardous Substances Data: 262849-67-2(Hazardous Substances Data)

Usage

Functional groups

Bromo and cyano The presence of a bromine atom (bromo) and a cyano group (CN) in the molecule contributes to its reactivity and utility in chemical reactions.

Structure

2,3,4,6-Tetra-O-benzoyl-1-deoxy-beta-D-glucopyranosyl The compound has a core structure of a beta-D-glucopyranose ring, with four benzoyl groups attached to the 2, 3, 4, and 6 positions, and a cyanide group at the anomeric carbon (1-position).

Application

Building block in complex carbohydrate synthesis This compound is used as a starting material for the synthesis of complex carbohydrates and glycoconjugates, which are important biomolecules in living organisms.

Use in stereoselective glycosylation

The compound is often employed in organic chemistry and chemical biology as a reagent for the stereoselective glycosylation of various substrates, allowing for the formation of specific glycosidic bonds with high selectivity.

Hazardous and toxic properties

It is important to handle 2,3,4,6-Tetra-O-benzoyl-1-bromo-1-deoxy-beta-D-glucopyranosyl cyanide with care, as it can be hazardous and toxic if not used properly. This is due to the presence of the cyano group, which can release highly toxic hydrogen cyanide (HCN) upon hydrolysis or in the presence of acid.

Upstream product

• 286369-05-9 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide 

Relevant articles and documents

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

A new, scalable preparation of a glucopyranosylidene-spiro- thiohydantoin: One of the best inhibitors of glycogen phosphorylases

Benzobromo-glucose was converted into per-O-benzoylated β-D- glucopyranosyl cyanide by mercury(II) cyanide in nitromethane. Partial hydrolysis of the nitrile with hydrogen bromide in acetic acid gave per-O- benzoylated C-(β-D-glucopyranosyl)formamide. Photobromination using bromine in carbon tetrachloride, chloroform, or dichloromethane gave the corresponding per-O-benzoylated 1-bromo-1-deoxy-β-D-glucopyranosyl cyanide and C-(1-bromo-1-deoxy-β-D-glucopyranosyl)formamide. Reaction of the latter with ammonium thiocyanate in nitromethane gave the per-O-benzoylated C-6S configured glucopyranosylidene-spiro-thiohydantoin together with a small amount of the per-O-benzoylated C-(1-hydroxy-β-D-glucopyranosyl)formamide. Debenzoylation of the spiro-thiohydantoin with sodium methoxide in methanol gave gram amounts of the title inhibitor. The described sequence should be suitable for scaling up and the target compound can be prepared in ~30% overall yield starting from D-glucose. (C) 2000 Elsevier Science Ltd.