beta-Glycosides of 2,3-Diazido-2,3-dideoxy-D-mannose, a Synthetic Precursor of a Rare Bacterial Cell-Wall Building Unit.
2,3-Diazido-2,3-dideoxy-beta-D-mannopyranoside derivatives were synthesized in order to prepare beta-glycosides of 2,3-diacetamido-2,3-dideoxy-D-mannuronic acid, a rare moiety of bacterial oligosaccharides. A direct glycosyl donor, 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-alpha-D-mannopyranosyl bromide, was prepared, and its synthetic capacity was tested in glycosylation reactions. An indirect route was also elaborated: 3-azido-3-deoxy-beta-D-glucopyranosides were converted into beta-D-mannopyranosides. The cis vicinal diazido function successfully tolerated the conditions of mild acidic hydrolysis, tritylation, Jones oxidation, TEMPO oxidation, acetolysis, and bromination with TiBr(4).
Szurmai
Z
Equipe "Endotoxines" du C.N.R.S. (U.R.A. 1116), Université de Paris-Sud, Centre d'Etudes Pharmaceutiques, 92296 Châtenay-Malabry, France, and Institute of Biochemistry, Faculty of Sciences, University of Debrecen, P.O. Box 55, H-4010 Debrecen, Hungary.
Rákó
J
Ágoston
K
Danan
A
Charon
D