One-pot oligosaccharide synthesis exploiting solvent reactivity effects.
[reaction: see text] One-pot syntheses of trisaccharides have been accomplished simply by changing the solvent system between the two subsequent glycosylation reactions and utilizing the difference in glycosylation rate between different solvents. By tuning the reactivity of acceptors and donors and performing the first glycosylation in Et(2)O (low glycosylation rate) and the second in CH(2)Cl(2)/Et(2)O (higher glycosylation rate), trisaccharides were synthesized in high yields (76-84%).
Lahmann
M
M
Department of Organic Chemistry, Arrhenius Laboratory, Floor 6, Stockholm University, S-106 91 Stockholm, Sweden.
Oscarson
S
S
D002240:Carbohydrate Sequence; D006031:Glycosylation; D007700:Kinetics; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012997:Solvents; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry
D009844:Oligosaccharides; D012997:Solvents; D014312:Trisaccharides