Photobromination of carbohydrate derivatives. Part 8. Reaction of furanose derivatives with N-bromosuccinimide. X-Ray molecular structure of 1-O-acetyl-2,5,6-tri-O-benzoyl-4-hydroxy-3,4-O-(α-succinimidobenzylidene)-β-D-galactofuranose

Abstract

Photobromination of 1-O-acetyl-2,3,5,6-tetra-O-benzoyl-β-D-gluco- or -galacto-furanose with N-bromosuccinimide gives the title compound in good yield. This was characterised by X-ray diffraction analysis, and analogous products were obtained by use of N-bromophthalimide or N-bromoacetamide. Similar reaction of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, pentabenzoyladenosine, and 1,2,3,4-tetra-O-acetyl-β-D-xylopyranose gave no such products but, instead, the corresponding 4-, 4-, and 5-bromide, respectively.

The title compound was efficiently converted into 1-O-acetyl-2,3,5,6-tetra-O-benzoyl-4-chloro-β-D-glucofuranose.