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Título : Synthesis of polyhydroxylated 2H-azirines and 2-halo-2H-azirines from 3-azido-2,3-dideoxyhexopyranoses by alkoxyl radical fragmentation
Autor : Alonso-Cruz, Carmen R., Kennedy, Alan R., Rodríguez Morales, María S., Suárez, Ernesto
Fecha de publicación : 26-Apr-2008
Editor: American Chemical Society
Resumen: 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.
Descripción : 7 pages, 4 tables, 1 scheme.-- PMID: 18439022 [PubMed].-- Printed version published Apr 26, 2008.
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ISSN: 0022-3263
DOI: 10.1021/jo800182y
Citación : Journal of Organic Chemistry 73(11): 4116-4122 (2008)
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