The Synthesis of Some Octenoses as Potential Precursors to Lincosamine, a Derived Portion of the Antibiotic Lincomycin

Abstract

Methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside, a potential precursor to lincosamine, has been prepared from both methyl α-D-galactopyranoside and methyl α-D-glucopyranoside, with the required inversion at C4 in the latter sequence being effected by a conventional oxidation-reduction. As well, (E)-6,7-dideoxy-1,2: 3,4-di-O-isopropylidene-α-D-galacto-oct-6-enose and (E)- and (Z)-6,7,8- trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enose have been prepared from 1,2: 3,4-di-O-isopropylidene-α-D-galactose.