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

The 4-O-sulfuric esters of methyl 6-deoxy-alpha-L-talo- and -alpha-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 H-1- and C-13-NMR data are given and discussed.