Glycal scavenging in the synthesis of disaccharides using mannosyl iodide donors

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22 Scopus citations

Abstract

(Chemical Equation Presented) High mannose glycans composed of α (1→2) and α (1→6) branched sugars are important components of the HIV-associated envelope glycoprotein, gp120. These substructures can be efficiently prepared in solution from glycosyl iodide precursors requiring only a slight excess of the iodide donor, which offers advantages over solid-phase methods that require more than 5 equiv of donor. During the reaction, excess iodide is converted to a glycal that is not easily separated from the desired disaccharide. To overcome this difficulty, a phase-trafficking methodology that relies upon nucleophilic interception of the 1,2 anhydrosugar resulting from oxidation of the glycal has been developed.

Original languageEnglish (US)
Pages (from-to)2387-2390
Number of pages4
JournalJournal of Organic Chemistry
Volume70
Issue number6
DOIs
StatePublished - Mar 18 2005

ASJC Scopus subject areas

  • Organic Chemistry

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