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Closed Access item 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
Appears in Collections:(IPNA) Artículos

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