Collect. Czech. Chem. Commun. 2000, 65, 1737-1744

Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses

Petr Bartoš, Miloslav Černý*, Iva Tišlerová and Tomáš Trnka

Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic


A novel method for the synthesis of unsaturated sulfur-linked (1→4)-disaccharides is described. The starting 1,6-anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose (3) was reacted with potassium salt of acetylated 1-thiohexopyranoses of D-gluco-, D-galacto-, and L-galacto-configuration to give acetylated β-glycopyranosyl-(1→4)-1,6-anhydro-2,3-dideoxy-4-thio-β-D-erythro-hex-2-enopyranoses 8-10. Their acid methanolysis under mild conditions afforded the corresponding methyl glycosides 11-13. The structure of new compounds was confirmed by 1H NMR and mass spectra data.

Keywords: Carbohydrates; Thiosugars; Unsaturated sulfur-linked dissaccharides; 1,6-Anhydrohexopyranoses; Nucleophilic substitutions; Allylic rearrangement; 1H NMR spectroscopy; Mass spectrometry.

References: 25 live references.