An alternative route to 2-deoxysugar and 2,3-unsaturated sugar derivativesvia the corresponding 1-nitro-1-alkenes

Authors
Koos, M
Citation
M. Koos, An alternative route to 2-deoxysugar and 2,3-unsaturated sugar derivativesvia the corresponding 1-nitro-1-alkenes, TETRAHEDR L, 41(28), 2000, pp. 5403-5406
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
28
Year of publication
2000
Pages
5403 - 5406
Database
ISI
SICI code
0040-4039(20000708)41:28<5403:AART2A>2.0.ZU;2-V
Abstract
An efficient method for the preparation of suitably O-protected 2-deoxysuga r oximes starting from corresponding sugar 1-nitro-1-alkenes and using tin( II) chloride as a reducing agent is described. The prepared oximes were fur ther transformed into either free 2-deoxysugars or 2-deoxysugar nitriles an d acids. 2,3-Unsaturated sugar oximes were also prepared starting from O-ac etylated sugar 1-nitroalkenes. The preparation of 2-deoxy-D-glucose is repr esentative. (C) 2000 Elsevier Science Ltd. All rights reserved.