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

Fingerprint

Sugar Alcohols
carbohydrates
Carbohydrates
Benzene
Iodine
Isomers
iodine
fragmentation
Carbon
isomers
benzene
Irradiation
Derivatives
X rays
irradiation
carbon
synthesis
configurations
x rays
alkoxyl radical

Keywords

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

Cite this

Francisco, C.G. ; Gonzalez, C.C. ; Kennedy, A.R. ; Paz, N.R. ; Suarez, E. / Fragmentation of carbohydrate anomeric alkoxyl radicals: synthesis of chiral 1-bromo-1-fluoro-1-iodo-alditols. In: Tetrahedron: Asymmetry. 2004 ; Vol. 15, No. 1. pp. 11-14.
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Fragmentation of carbohydrate anomeric alkoxyl radicals: synthesis of chiral 1-bromo-1-fluoro-1-iodo-alditols. / Francisco, C.G.; Gonzalez, C.C.; Kennedy, A.R.; Paz, N.R.; Suarez, E.

In: Tetrahedron: Asymmetry, Vol. 15, No. 1, 12.01.2004, p. 11-14.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Fragmentation of carbohydrate anomeric alkoxyl radicals: synthesis of chiral 1-bromo-1-fluoro-1-iodo-alditols

AU - Francisco, C.G.

AU - Gonzalez, C.C.

AU - Kennedy, A.R.

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AU - Suarez, E.

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AB - 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.

KW - 2-bromo-2-deoxy-2-fluoro-hexopyranose

KW - pentopyranose

KW - benzene

KW - iodine

KW - diastereoisomeric

KW - crystallographic

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DO - 10.1016/j.tetasy.2003.10.016

M3 - Article

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