SYNTHESIS OF β-D-RIBOPYRANOSIDES DERIVATIVES FROM β-D-XYLOPYRANOSIDE

Abstract: The aim of this thesis was to synthesize various β-D-ribopyranoside derivatives with different C-4 functional groups, using D-xylose as the starting material. The desired modifications were deoxygenation, fluorination, methylation and epimerization of the C-4 hydroxyl group. Methylation provided the best results with the final product being successfully synthesized. Deoxygenation was also achieved but the final de-protection step was not carried out. Epimerization was attempted using two different methods but without success, firstly probably due to the high energetic favorability of having the hydroxyl group in the equatorial position, and secondly due to harsh reaction conditions causing the cleavage of the hydroxyl group. Fluorination was not attempted.