Stereoselective Synthesis ofN-(α- and β-Ribofuranosyl)-Formamtdes and Related Glycosyl Formamtdes - Precursors for Sugar Isocyantdes

Abstract

Abstract Efficient stereospecific N-formylation of ribosylamine has been achieved, affording the α-anomer directly (by reaction with formic-acetic anhydride) and the β-anomer via the corresponding formamidine derivative (by reaction with dimethylformamide dimethyl acetal). Dehydration of the α-anomer gave the corresponding isocyanide without compromising the anomeric purity. The amidine route was extended to give the N-formyl derivatives of α-xylosylamine and α-arabinosylamine.