Synthesis and Structure of Novel Glycoside and Nucleoside Derivatives of Phospha Sugar Analogs

Abstract

The synthesis and structure of novel glycoside and nucleoside derivatives of phospha sugar analogs from phospholenes are reported. 1-Phenyl-2-phospholene 1-oxide was regio-and diastereo-selectively converted into a 2-bromo-3-hydroxyphospholane derivative by an action of bromine in aqueous media. The reaction of the 2-bromophospholane derivative with some amines afforded 2-amino derivatives, which were N-glycosides of phospha sugar analogs. The 2-bromophospholane derivative was also converted into the corresponding azido derivative by the replacement of the 2-bromo substituent with sodium azide. 1,3-Diploar cycloaddition of the azido derivative with alkynes afforded phospha sugar nucleoside analogs which have a triazole ring as a nitrogen heterocycle.