Diastereoselective propargylation of sugar aldehydes. New synthesis of 6-deoxyheptoses

Article abstract of DOI:10.1016/S0040-4020(96)01156-8

Propargylation of pentofuranose aldehydes by treatment with propargyl bromide in the presence of zinc dust yielded homopropargylic alcohols with a good isolated yield and, in many cases, excellent anti/syn selectivity. Catalytic hydrogenation of the triple bond afforded homoallylic alcohols, valuable substrates for the synthesis of 6-deoxyheptoses. Direct ozonolysis of the triple bond yielded uronic acid esters.