Mitsunobu glycosylation of nitrobenzenesulfonamides: Novel route to Amadori Rearrangement Products

Citation
Jj. Turner et al., Mitsunobu glycosylation of nitrobenzenesulfonamides: Novel route to Amadori Rearrangement Products, TETRAHEDR L, 40(38), 1999, pp. 7039-7042
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
38
Year of publication
1999
Pages
7039 - 7042
Database
ISI
SICI code
0040-4039(19990917)40:38<7039:MGONNR>2.0.ZU;2-F
Abstract
Amino-acid derived 2-nitrobenzenesulfonamides were successfully condensed u nder Mitsunobu conditions with 2,3,4,6-tetra-O-acetyl-D-glucose to afford t he fully protected glucosylamines in excellent yield. Upon total deprotecti on, these compounds rearranged to provide the corresponding Amadori product s in good overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved .