Collect. Czech. Chem. Commun. 1985, 50, 1291-1299

Synthesis of 2,3,5-tri-O-benzoyl-D-pentofuranosyl cyanides and their CD spectra

Jiří Farkaš and Ivo Frič

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


The title compounds I-IV with the respective ribo-, arabino-, xylo- and lyxo-configuration were prepared by reaction of 1-O-acetyl-2,3,5-tri-O-benzoyl-D-pentofuranoses with trimethylsilyl cyanide in 1,2-dichloroethane, catalyzed with tin tetrachloride. The CD spectra of compounds I-IV and of the conformationally rigid 1,5-anhydro-2,3-di-O-benzoyl-β-D-pentofuranoses VI-VIII were measured and interpreted by the exciton chirality method.