Novel aldol-type cyclocondensation of O-mesyl (methylsulphonyl) cyanohydrins. Application to the stereospecific synthesis of branched-chain sugars

Abstract

Reaction of O-mesylcyanohydrins of furanos-3-uloses with base afforded furanose-3-spiro-5′-[4′-amino-1′,2′-oxathiole-2′,2′-dioxide] derivatives, which on treatment with MeONa/MeOH gave C-[(E)-2-(methoxysulphonyl)-1-(amino)-vinyl] branched-chain sugars, having the same configuration as the starting cyanohydrins.