Regioselective Alkylation of Alcohols from the Bis-heterocyclic SMe-Pyrimidino-Pyranoside Platform

Abstract

This work contributes to the synthesis of new bis-heterocyclic platforms based on carbohydrates and nitrogenous heterocycles and to the study of their functionalization with a view to obtaining compounds of therapeutic interest. The study of the reactivity of the SMe-pyrimidino-pyranoside platform has enabled us to propose a new route for introducing spacer arms capable of mimicking natural peptides. The functionalization of the pyranose moiety was studied by benzylidene cleavage followed by regioselective alkylation of the alcohol in the 4 or 6-position via a 4,6-O-stannylene intermediate using dibutyltin oxide (Bu2SnO). Finally, this SMe-pyrimidino-pyranoside platform offers opportunities for introducing molecular diversity and appears to be an interesting tool for constructing biologically active molecules.