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Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/12618
Title: Synthesis of polyhydroxylated 2H-azirines and 2-halo-2H-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation
Authors: Alonso-Cruz, Carmen R. ; Kennedy, Alan R.; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date: 26-Apr-2008
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry 73(11): 4116-4122 (2008)
Abstract: The reaction of 3-azido-2,3-dideoxypyranose and 3-azido-2,3-dideoxy-2-halohexopyranose compounds with (diacetoxyiodo)benzene and iodine generated 2-azido-1,2-dideoxy-1-iodoalditols and 2-azido-1,2-dideoxy-1-halo-1-iodoalditols, respectively. These β-iodo azides could be transformed by chemoselective dehydroiodination into 2-azido-1,2-dideoxy-4-O-formyl-pent-1-enitols and (Z,E)-2-azido-1,2-dideoxy-1-halo-4-O-formyl-pent-1-enitols in good yields. Thermolysis and photochemical studies of these vinyl azides and 1-halovinyl azides for the synthesis of polyhydroxylated 3-alkyl-2H-azirines and the hitherto unknown 2-halo-3-alkyl-2H-azirines have also been accomplished.
Description: 7 pages, 4 tables, 1 scheme.-- PMID: 18439022 [PubMed].-- Printed version published Apr 26, 2008.
Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo800182y
Publisher version (URL): http://dx.doi.org/10.1021/jo800182y
URI: http://hdl.handle.net/10261/12618
DOI: 10.1021/jo800182y
ISSN: 0022-3263
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