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

Abstract

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.