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Title

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

AuthorsFrancisco, Cosme G. ; González Martín, Concepción C. ; Kennedy, Alan R.; Rodríguez Paz, Nieves
Issue Date12-Jan-2004
PublisherElsevier
CitationTetrahedron Asymmetry 15(1): 11-14 (2004)
AbstractThe reaction of 2-bromo-2-deoxy-2-fluoro-hexopyranose and -pentopyranose compounds from the d-gluco, d-galacto, l-rhamno, l-fuco, and l-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 d-galacto derivative, the diastereoisomeric mixture can be chromatographically separated and the absolute configuration determined by X-ray crystallographic analysis of the (1R)-isomer.
Description4 pages, 1 table, 1 scheme.-- Available online Dec 3, 2003.
Publisher version (URL)http://dx.doi.org/10.1016/j.tetasy.2003.10.016
URIhttp://hdl.handle.net/10261/16756
DOI10.1016/j.tetasy.2003.10.016
ISSN0957-4166
Appears in Collections:(IPNA) Artículos
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