NDLI: Fragmentation of Carbohydrate Anomeric Alkoxyl Radicals: New Synthesis of Chiral 1-Fluoro-1-halo-1-iodoalditols

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Fragmentation of Carbohydrate Anomeric Alkoxyl Radicals: New Synthesis of Chiral 1-Fluoro-1-halo-1-iodoalditols

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Fragmentation of Carbohydrate Anomeric Alkoxyl Radicals: New Synthesis of Chiral 1-Fluoro-1-halo-1-iodoalditols

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Francisco, Cosme G. Paz, Nieves R. Suárez, Ernesto Kennedy, Alan R. González, Concepción C.
Description	Author Affiliation: Francisco CG ( Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Cientificas, Carretera de La Esperanza 3, La Laguna, Tenerife, Spain. ccgm@ipna.csic.es)
Abstract	A new general methodology for the synthesis of 1,1,1-trihaloalditols by starting from 1,5-anhydro-2-deoxy-hex-1-enitol derivatives (glycals) is described. The halogens are introduced sequentially in each of the three different steps of the process. The fluorine is introduced in the first step by electrophilic fluorination of the starting glycal; next, hydroxyhalogenation of the resulting vinyl fluoride allows the addition of any halogen (F, Cl, Br or I) at will, and finally, an iodine atom is inserted through an alkoxyl radical fragmentation reaction. This methodology allows the preparation of diverse types of 1,1,1-trihalogenated compounds $(RCF_{2}I,$ $RCFI_{2},$ RCFClI and RCFBrI) under mild conditions compatible with sensitive substituents. In some cases, the diastereomeric mixtures generated from RCFClI and RCFBrI can be chromatographically separated, and their configuration determined by X-ray crystallographic analysis. The synthetic usefulness of these compounds has been preliminarily assessed by examining the reactivity of the fluorinated radical generated by rupture of the CI bond.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	22
Volume Number	14
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2008-01-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Sugar Alcohols Chemical Synthesis Crystallography, X-Ray Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Spectrometry, Mass, Electrospray Ionization Stereoisomerism Chemistry Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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