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Reaction of 2-bromo-3-hydroxy-1-methoxy-3-methylphospholane 1-oxide with silylated 2-hydroxypyridine gave a novel non-natural phosphono sugar nucleoside derivative.

Treatment of 1-phenyl-2-phospholene 1-oxide with N-bromoacetamide or bromine afforded threo and erythro bromohydrins, the latter being converted into novel N-glycosides by reaction with amines. The N-t-butyl phosphono sugar glycoside exists in the 2E conformation.

Treatment of 1-phenyl-2-, and -3-phospholene 1-oxides with N-bromosuccinimide affords 4-bromo-1-phenyl-2-phospholene 1-oxide. Substitution of the bromide with acetate, followed by stereoselective oxidation with osmium tetroxide and peracetylation with acetic anhydride/pyridine affords phospho sugar derivatives of tetrafuranose. Furthermore, N-, O-, and S-glycosyl compounds of phospho sugars can be prepared from 3-methyl-1-phenyl-2-phospholene 1-oxide by bromination and nucleophilic substitution reactions. This is a novel and excellent route to prepare phospho sugar derivatives