title: Protecting-group-free synthesis of glycosyl 1-phosphates.
abstract: Glycosyl 1-phosphates enriched in the α-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.
authors: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
authors: Landon John G
authors: LJ
authors: Edgar
authors: Somnath
authors: S
authors: Dasgupta
authors: Mark
authors: M
authors: Nitz
mesh_terms: D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D010755:Organophosphates / Q000138:chemical synthesis* / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006027:Glycosides; D010755:Organophosphates; D010756:Phosphoric Acids; D003300:Copper; C030242:phosphoric acid; C029892:cupric chloride