Fragmentation of carbohydrate anomeric alkoxyl radicals: synthesis of chiral 1-bromo-1-fluoro-1-iodo-alditols

Francisco, C.G. and Gonzalez, C.C. and Kennedy, A.R. and Paz, N.R. and Suarez, E. (2004) Fragmentation of carbohydrate anomeric alkoxyl radicals: synthesis of chiral 1-bromo-1-fluoro-1-iodo-alditols. Tetrahedron: Asymmetry, 15 (1). pp. 11-14. ISSN 0957-4166 (http://dx.doi.org/10.1016/j.tetasy.2003.10.016)

Abstract

The reaction of 2-bromo-2-deoxy-2-fluoro-hexopyranose and -pentopyranose compounds from the -gluco, -galacto, -rhamno, -fuco, and -arabino carbohydrate series with (diacetoxyiodo)benzene and iodine, under visible light irradiation conditions, generated the corresponding 1-bromo-1-deoxy-1-fluoro-1-iodo-alditols with one less carbon. In the case of the -galacto derivative, the diastereoisomeric mixture can be chromatographically separated and the absolute configuration determined by X-ray crystallographic analysis of the (1R)-isomer.

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• Item metadata

  Item type:	Article
  ID code:	1008
  Dates:	Date Event 12 January 2004 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry Faculty of Engineering > Electronic and Electrical Engineering
  Depositing user:	Users 45 not found.
  Date deposited:	09 May 2006
  Last modified:	08 Apr 2024 15:31
  URI:	https://strathprints.strath.ac.uk/id/eprint/1008