Efficient synthesis of man2, man3, and man 5 oligosaccharides, using mannosyl iodide donors

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Abstract

A highly efficient protocol for making Man3 and Man5 oligosaccharides with use of orthogonally protected glycosyl iodide donors has been developed. Glycosylation of a C-2-O-acetyl mannosyl iodide donor in the presence of silver triflate at -40 °C initially gave a mixture of the desired α-linked mannoside and an orthoacetate resulting from attack at the C-2 acetate. However, upon warming to room temperature the orthoacetate quantitatively rearranged to the desired oligosaccharide. Employing a 3,6-dihydroxy acceptor and subjecting it to double glycosidation quickly afforded high mannose sugars in nearly quantitative yields. Glycosyl iodide donors offer advantages over previously reported chloride donors as the reactions are faster, proceed in higher yields, and are not diminished in higher order constructs. These studies continue to dispel the notion that glycosyl iodides are too reactive to be of synthetic utility.

Original languageEnglish (US)
Pages (from-to)8772-8779
Number of pages8
JournalJournal of Organic Chemistry
Volume70
Issue number22
DOIs
StatePublished - Oct 28 2005

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Iodides
Oligosaccharides
Mannosides
Glycosylation
Mannose
Sugars
Chlorides
Acetates
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient synthesis of man2, man3, and man 5 oligosaccharides, using mannosyl iodide donors. / Lam, Son N.; Gervay-Hague, Jacquelyn.

In: Journal of Organic Chemistry, Vol. 70, No. 22, 28.10.2005, p. 8772-8779.

Research output: Contribution to journalArticle

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