69534-61-8

Basic information

• Product Name: 1,2,3,4,6-Penta-O-acetyl-5-bromo-β-D-glucopyranose
• Synonyms: 1,2,3,4,6-Penta-O-acetyl-5-bromo-β-D-glucopyranose
• CAS NO: 69534-61-8
• Molecular Weight: 469.24
• Mol File: 69534-61-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2,3,4,6-Penta-O-acetyl-5-bromo-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4,6-Penta-O-acetyl-5-bromo-β-D-glucopyranose(69534-61-8)
• EPA Substance Registry System: 1,2,3,4,6-Penta-O-acetyl-5-bromo-β-D-glucopyranose(69534-61-8)

Safety Data

• Hazardous Substances Data: 69534-61-8(Hazardous Substances Data)

Upstream product

• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 127381-77-5 Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-seleno<5-²H>-D-arabino-hexopyranoside 
• 127381-86-6 Phenyl 3,4,6-Tri-O-acetyl-2-deoxy-1-seleno<5-²H>-D-arabino-hexopyranoside 

Relevant articles and documents

Photo-bromination of Carbohydrate Derivatives. Part 2.. Penta-O-acetyl-β-D-glucopyranose; the 5-Bromo-derivative and Products of Further Bromination

Photo-bromination of penta-O-acetyl-β-D-glucopyranose with N-bromosuccinimide in carbon tetrachloride causes specific replacement of H-5, and the 5-bromo-derivative can be isolated crystalline in high yield.By-products of the reaction contain monobromoacetyl and dibromoacetyl groups.When bromine was used as reagent the 5-substituted compound was again formed as initial product, but, ultimately, tetra-O-acetyl-α-D-glucopyranosyl bromide and dibromides with halogen substituents at C-1 and C-5, and with both bromine atoms at C-1, were also produced.A two-step route from glucose penta-acetate to 1,2,3,4-tetra-O-acetyl-6-deoxy-β-D-xylo-hex-5-enose is defined.Since the C-5 epimer of the penta-acetate affords the same products, it is proposed that the initial bromination proceeds by way of a discrete radical at the tertiary site.