SYNTHESIS OF 5-THIO-D-ARABINOSE AND 5-THIO-D-LYXOSE AND THEIR METHYL GLYCOPYRANOSIDES

Article abstract of DOI:10.1016/0008-6215(85)85213-7

1,2-O-Isopropylidene-5-O-toluene-p-sulpholyl-β-D-arabinofuranose has been converted into 5-thio-D-arabinose via 3-O-acetyl-5-S-acetyl-1,2-O-isopropylidene-5-thio-β-D-arabinofuranose. 5-Thio-D-lyxose was similarly obtained from methyl 2,3-O-isopropylidene-5-O-methanesulpholyl(or toluene-p-sulphonyl)-α-D-lyxofuranoside via methyl 5-S-acetyl(or benzoyl)-1,2-O-isopropylidene-5-thio-α-D-lyxofuranoside.The corresponding methyl thiopyranosides were obtained by mehanolysis of the free sugars or the above thioester intermediates.All the 5-thio-D-pentopyranoses and their methyl 5-thio-D-pentopyranosides are now known, and some of their properties are summarised.