NOVEL REARRANGEMENT REACTIONS IN THE FLUORINATION OF METHYL 3-C-METHYL-3-NITRO-ALPHA-L-HEXOPYRANOSIDES BY THE DAST REAGENT

Authors
BORRACHEROMOYA P CABRERAESCRIBANO F GOMEZGUILLEN M MADRIDDIAZ F
Citation
P. Borracheromoya et al., NOVEL REARRANGEMENT REACTIONS IN THE FLUORINATION OF METHYL 3-C-METHYL-3-NITRO-ALPHA-L-HEXOPYRANOSIDES BY THE DAST REAGENT, Tetrahedron letters, 38(7), 1997, pp. 1231-1234
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
7
Year of publication
1997
Pages
1231 - 1234
Database
ISI
SICI code
0040-4039(1997)38:7<1231:NRRITF>2.0.ZU;2-J
Abstract
A simple method for the preparation of 1-fluoro- and/or 5-fluoro-3-bra nched-chain sugar derivatives by reaction of DAST with methyl 3-C-meth yl-3-nitro-alpha-L-hexopyranosides is described. The reaction involves rearrangement with or without ring contraction, depending on the 1,2 relative configuration and the presence of a free OH group at C-4 in t he substrate. A new, useful aldehydo-sugar ramified at 0-3 is easily a ccessible in good yield by the route reported here. (C) 1997, Elsevier Science Ltd.