262849-68-3

Basic information

• Product Name: C-(2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL) FORMAMIDE
• Synonyms: C-(2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL) FORMAMIDE;C-(2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-SS-D-GLUCOPYRANOSYL) FORMAMIDE;C-(1-Bromo-1-deoxy-2,3,4,6-tetra-O-benzoyl-b-D-glucopyranosyl)formamide
• CAS NO: 262849-68-3
• Molecular Formula: C₃₅H₂₈BrNO₁₀
• Molecular Weight: 687.51006
• Mol File: 262849-68-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 810.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.52±0.1 g/cm3(Predicted)
• PKA: 13.17±0.70(Predicted)
• CAS DataBase Reference: C-(2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL) FORMAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: C-(2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL) FORMAMIDE(262849-68-3)
• EPA Substance Registry System: C-(2,3,4,6-TETRA-O-BENZOYL-1-BROMO-1-DEOXY-BETA-D-GLUCOPYRANOSYL) FORMAMIDE(262849-68-3)

Safety Data

• Hazardous Substances Data: 262849-68-3(Hazardous Substances Data)

Upstream product

• 262849-67-2 2,3,4,6-tetra-O-benzoyl-1-bromo-1-deoxy-β-D-glucopyranosyl cyanide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 286369-05-9 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide 
• 286369-06-0 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonamide 

Downstream Products

• 227458-60-8 (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione 

Relevant articles and documents

Chemoselective hydration of glycosyl cyanides to C-glycosyl formamides using ruthenium complexes in aqueous media

[RuCl2(DMSO)4] in the presence of N-benzylated 1,3,5-triaza-7-phosphaadamantane efficiently catalyzed the hydration of glycosyl cyanides to the corresponding formamide derivatives in water or water-N-methylpyrrolidone solvent mixture

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.