Protecting group free glycosidations using p-toluenesulfonohydrazide donors.
N'-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acetylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired beta- d-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired alcohol or transformed to the oxazoline or glycosyl azide.
Gudmundsdottir
Anna V
AV
Department of Chemistry, University of Toronto, Toronto, ON, Canada. mnitz@chem.utoronto.ca
Nitz
Mark
M
D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
D001386:Azides; D006027:Glycosides; D010080:Oxazoles; D014105:Tosyl Compounds; C002030:4-toluenesulfonyl hydrazide