New chirons from D-glucose. Regio- and diastereoselective carbon-carbon bond-forming reactions exploiting novel aldotetrofuranose acetates as chiral synthetic equivalents of tartaric aldehydes

Two differentially protected tetrafuranose axerates 5 and 6 have beenn prepared from diacetone D-gluccee in parallell short, routes. They clearly act as chiral synthetic equivalents of D- and tartaric aldehyde when exploited in Lewia acid promoted reactions with silicon-bases nucleophiles. The synthesis of immediate precursors of 2-deoxy-L-hexoses is presented as an application.