Synthesis of unsaturated sulfur-linked (1 -> 4)-disaccharides by substitution of tosyloxy group in 1,6-anhydro-3,4-dideoxy-2-O-tosyl-beta-D-erythro-hex-3-enopyranose with 1-thiohexopyranoses

摘要

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-beta -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 beta -glycopyranosyl-(1-->4)-1,6-anhydro-2,3-dideoxy-4-thio-beta -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 H-1 NMK and mass spectra data. [References: 25]