Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 39, Pages 10453-10456Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405084
Keywords
glycosylation; hydrogen bonds; oligosaccharides; protecting groups; synthetic methodology
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Funding
- NSF [CHE-1058112, CHE-0959360]
- Mizutani Foundation for Glycosciences [130057]
- University of Missouri, St. Louis Graduate School
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1058112] Funding Source: National Science Foundation
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A Hydrogen bond mediated aglycone delivery (HAD) method was applied to the synthesis of alpha-glucans, which are abundant in nature, but as targets represent a notable challenge to chemists. The synthesis of linear oligosaccharide sequences was accomplished in complete stereoselectivity in all glycosylations. The efficacy of HAD may diminish with the increased bulk of the glycosyl acceptor, and may be an important factor for the syntheses of oligomers beyond pentasaccharides. The synthesis of a branched structure proved more challenging, particularly with bulky trisaccharide acceptors.
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