Application of glycals to the synthesis of oligosaccharides: Convergent total syntheses of the Lewis X trisaccharide sialyl Lewis X antigenic determinant and higher congeners

Samuel J. Danishefsky, Jacquelyn Gervay-Hague, John M. Peterson, Frank E. McDonald, Koshi Koseki, David A. Griffith, Takeshi Oriyama, Stephen P. Marsden

Research output: Contribution to journalArticle

80 Scopus citations

Abstract

Exploiting the differences in reactivity of the hydroxyl groups of glucal allows for rapid access to the sLex tetrasaccharide glycal. This compound is readily converted to the title compounds by azaglycosylation followed by deprotection. The use of stannyl alkoxides in the glycosylation - rearrangement step allows for the use of minimally protected glycosides as the glycosyl acceptors. Employing a galactal epoxide as a glycosyl donor allows for a maximally convergent synthesis of the Lex glycal.

Original languageEnglish (US)
Pages (from-to)1940-1953
Number of pages14
JournalJournal of the American Chemical Society
Volume117
Issue number7
StatePublished - Feb 22 1995
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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