A STEREOSELECTIVE SYNTHESIS OF METHYL d-GLUCOSAMINATE VIA TIN(II) ENEDIOLATE FORMED FROM FURYLGLYOXAL

Abstract

The tin(II) enediolate, formed in situ from furylglyoxal, reacts with polyoxyaldehydes such as 2,3-O-isopropylidene-d-glyceraldehyde and 4-O-benzyl-2,3-O-isopropylidene-l-threose to give the cross aldol adducts in good yields. This reaction is successfully applied to the synthesis of methyl d-glucosaminate.