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Science 28 May 1993:
Vol. 260. no. 5112, pp. 1307 - 1309
DOI: 10.1126/science.8493573
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Articles

Science, Vol 260, Issue 5112, 1307-1309
Copyright © 1993 by American Association for the Advancement of Science

articles

A strategy for the solid-phase synthesis of oligosaccharides

SJ Danishefsky, KF McClure, JT Randolph, and RB Ruggeri

Department of Chemistry, Yale University, New Haven, CT 06511.

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.


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