Novel synthesis and structures of amines and triazole-derived glycoside and nucleoside derivatives of phosphanyl sugar analogs

3-Methyl-1-phenyl-2-phospholene and 1-phenyl-2-phospholene 1-oxides were co nverted into 2-bromo-3-hydroxy-3-methyl-1-phenylphospholane and 2-bromo-3-h ydroxyl-1-phenylphospholane 1-oxide (1-bromo-1,3,4-trideoxy-1,4-C-[(R, S)-p henylphosphinylidene]-glycero-tetrofuranose) by the action of bromine in aq ueous medium. The bromo substituent of the phospholane was substituted by t reatment with amines or an azide anion to afford novel glycoside derivative s of phosphanyl sugar analogs such as 2-ammo-3-hydroxy-1-phenylphaspholane (3,4-dideoxy-1,4-C-[(R, S)-phenylphosphinylidene]-glycero-tetrofuranosylami ne) and 2-azido-3-hydroxy-3-methyl-1-phenylphospholane 1-oxides with retent ion of the configuration. The 1,3-dipolar cycloaddition of the 2-azido deri vative of the phospholane with alkynes gave 3-hydroxy-3-methyl-1-phenyl-2-( triazol-1-yl)phospholane 1-oxides as a novel triazole-derived nucleoside of phosphanyl sugar analogs. The structure of the glycoside and nucleoside de rivatives of the phosphanyl sugar analogs prepared was deterimined from IR, NMR, and X-ray crystallography analysis.