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Synthesis of ss-(1 -> 2)-Linked 6-Deoxy-L-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 5
2017 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 6, 3062-3071 p.Article in journal (Refereed) Published
Abstract [en]

The ss-(1 -> 2)-linked 6-deoxy-L-altropyranose di- to pentasaccharides 2-5, relevant to the O-antigen of the infectious Yersinia enterocolitica 0:3, were synthesized for the first time. The challenging 1,2-cis-altropyranosyl linkage was assembled effectively via glycosylation with 2-O-benzyl-3,4-di-O-benzoyl-6-deoxy-L-altropyranosyl ortho-hexynylbenzoate (7) under the catalysis of PPh3AuNTf2. NMR and molecular modeling studies showed that the pentasaccharide (5) adopted a left-handed helical conformation. [GRAPHICS]

Place, publisher, year, edition, pages
2017. Vol. 82, no 6, 3062-3071 p.
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Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-142654DOI: 10.1021/acs.joc.7b00057ISI: 000397077500026PubMedID: 28230982OAI: oai:DiVA.org:su-142654DiVA: diva2:1095179
Available from: 2017-05-12 Created: 2017-05-12 Last updated: 2017-05-12Bibliographically approved

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