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.
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