Synthesis of methyl 6-deoxy-4-O-(sodium sulfonato)-α -L-talopyranoside, its C-4 epimer and both isosteric [4-C-(potassium sulfonatomethyl)] derivatives

Abstract

The 4-O-sulfuric esters of methyl 6-deoxy-α-L-talo- and -α-L-mannopyranoside were prepared. The first ester is a component of the glycopeptidolipid-type cell surface antigens of M. avium. The isosteric isomers (sugar-4-CH2-SO3Na) of both sulfate esters (sugar-4-O-SO3Na) were synthesized using free radical addition reactions between sugar-exomethylene derivatives and (either thioacetic acid or NaHSO3. The addition products of thioacetic acid were converted into) (sugar-CH2-sulfonic acids by oxidation with oxone. Characteristic 1H- and 13C-NMR data are) given and discussed.