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

C.G. Francisco, C.C. Gonzalez, A.R. Kennedy, N.R. Paz, E. Suarez

Research output: Contribution to journalArticle

14 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)11-14
Number of pages3
JournalTetrahedron: Asymmetry
Volume15
Issue number1
DOIs
Publication statusPublished - 12 Jan 2004

Keywords

  • 2-bromo-2-deoxy-2-fluoro-hexopyranose
  • pentopyranose
  • benzene
  • iodine
  • diastereoisomeric
  • crystallographic

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