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

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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)

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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.

ORCID iDs

Francisco, C.G., Gonzalez, C.C., Kennedy, A.R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Paz, N.R. and Suarez, E.;
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