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

Authors
Bartos, P Cerny, M Tislerova, I Trnka, T
Citation
P. Bartos et al., 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, COLL CZECH, 65(11), 2000, pp. 1737-1744
Citations number
25
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
00100765 → ACNP
Volume
65
Issue
11
Year of publication
2000
Pages
1737 - 1744
Database
ISI
SICI code
0010-0765(200011)65:11<1737:SOUS(->2.0.ZU;2-M
Abstract
A novel method for the synthesis of unsaturated sulfur-linked (1-->4)-disac charides 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 acetyla ted 1-thiohexopyranoses of D-gluco-, D-galacto-, and L-galacto-configuratio n 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 unde r mild conditions afforded the corresponding methyl glycosides 11-13. The s tructure of new compounds was confirmed by H-1 NMK and mass spectra data.