Sequential One-Pot Glycosylations Using 1-Hydroxyl and 1-Thiodonors

A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph2SO/Tf2O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator syst...

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Published inOrganic letters Vol. 5; no. 11; pp. 1947 - 1950
Main Authors Codée, Jeroen D. C, van den Bos, Leendert J, Litjens, Remy E. J. N, Overkleeft, Herman S, van Boom, Jacques H, van der Marel, Gijs A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.05.2003
Amer Chemical Soc
Subjects
Carbohydrate Sequence
Chemistry
Chemistry, Organic
Glycosylation
Indicators and Reagents
Molecular Sequence Data
Physical Sciences
Science & Technology
Trisaccharides - chemical synthesis
GLYCOSIDES
THIOGLYCOSIDES
ACTIVATION
OLIGOSACCHARIDE SYNTHESIS
REACTIVITY
DETERMINANT
DONORS
DERIVATIVES
TRIFLUOROMETHANESULFONIC ANHYDRIDE
STRATEGIES
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Summary:A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph2SO/Tf2O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The α-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol034528v