A strategy for the solid-phase synthesis of oligosaccharides.
Repeating glycosidic linkages of oligosaccharides can be synthesized by solid-phase methods. Glycals were attached to a polystyrene copolymer with a silyl ether bond and were activated to function as glycosyl donors with 3,3-dimethyldioxirane. Glycosidation was performed by reactions with a solution-based acceptor (itself a glycal). Excess acceptor and promoter were removed by rinsing after each coupling, and the desired oligosaccharides were then easily obtained from the polymer by the addition of tetra-n-butylammonium fluoride. By this method, glycosidations are stereospecific and interior deletions are avoided.
Danishefsky
S J
SJ
Department of Chemistry, Yale University, New Haven, CT 06511.
McClure
K F
KF
Randolph
J T
JT
Ruggeri
R B
RB
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004852:Epoxy Compounds / Q000737:chemistry; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011137:Polystyrenes
D004852:Epoxy Compounds; D009844:Oligosaccharides; D011137:Polystyrenes; C064455:dimethyldioxirane