A one-step beta-selective glycosylation of N-acetyl glucosamine and recombinant chitooligosaccharides

Authors
Vauzeilles, B Dausse, B Palmier, S Beau, JM
Citation
B. Vauzeilles et al., A one-step beta-selective glycosylation of N-acetyl glucosamine and recombinant chitooligosaccharides, TETRAHEDR L, 42(43), 2001, pp. 7567-7570
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
43
Year of publication
2001
Pages
7567 - 7570
Database
ISI
SICI code
0040-4039(20011022)42:43<7567:AOBGON>2.0.ZU;2-#
Abstract
N-Acetyl glucosamine and chitooligosaccharides are selectively converted in to beta -glycosides without protection of the other hydroxyl groups by alky lation of the anomeric alkoxides in N,N-dimethylformamide containing lithiu m bromide. Addition of the lithium salt notably improves the stereoselectiv ity of the glycosylation of the monomer and the efficiency of the process w ith higher oligomers. (C) 2001 Elsevier Science Ltd. All rights reserved.