Classical synthesis of a new class of compounds via coupling of sugars and amino acids

Abstract

A new class of pharmacologically interesting compounds has been synthesized through a novel S_N2 dispalcement of the CF₃SO₂ group in benzyl 2,3-anhydro-4-trifluoromethylsulphonyl-α-D-ribopyranoside (1) and its β-L-isomer (2), by a variety of suitably protected naturally occurring amino acids: the reaction pathway also provides an efficient route to benzyl 2,3-anhydro-β-L- and -α-D-lyxopyranosides [(3) and (4) respectively].