Regio-and stereoselective phosphonylation of sugars and its application for anti-cancer and anti-HIV agen

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Reaction of tri-O-acetylglucal with chloro (diisopropylamino) phosphenium cation gave 1-phosphonylated 2-eno-pyranoside stereo and regioselectivily. After deprotection, endothelin receptor binding accey of the deprotected phosphonylated sugar was investigated, but good results were not obtained.On the other hand, reaction of tri-O-acetylgulucal with diphenylphosphenium cation in dichloromethane, unsaturated sugars having phosphinoyl group on 1-and 3-position was obtained in 51% (1-alpha), 21% (1-beta), and 6% (3-peudaxial), respectively. The stereochemistry of these products were determined by their NOESY spectra. The ozonolysis of 1-phospinoyl-unsaturated sugar in dichloromethane at -78ﾟC gave dialdehyde which cyclyzed in intramolecular aldol-type reaction manner gave franoside in 41% yield. These results will be published elsewhere.