IODINE - A VERSATILE REAGENT IN CARBOHYDRATE-CHEMISTRY .2. EFFICIENT CHEMOSPECIFIC ACTIVATION OF THIOMETHYLGLYCOSIDE

Authors
KARTHA KPR ALOUI M FIELD RA
Citation
Kpr. Kartha et al., IODINE - A VERSATILE REAGENT IN CARBOHYDRATE-CHEMISTRY .2. EFFICIENT CHEMOSPECIFIC ACTIVATION OF THIOMETHYLGLYCOSIDE, Tetrahedron letters, 37(29), 1996, pp. 5175-5178
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
29
Year of publication
1996
Pages
5175 - 5178
Database
ISI
SICI code
0040-4039(1996)37:29<5175:I-AVRI>2.0.ZU;2-L
Abstract
Iodine has been found to be an efficient promoter in the alcoholysis o f unprotected or fully benzylated methyl I-thio-beta-D-galactopyranosi de. Stereoselective formation of 1,2-cis linkages in oligosaccharide s ynthesis using ''armed'' thiomethyl glycosides as glycosyl donors was also observed. Protecting groups such as acetate, benzoate, benzyliden e, isopropylidene, trimethylsilylethyl etc are stable under the reacti on conditions. Copyright (C) 1996 Elsevier Science Ltd