Synthesis of β‑(1→2)-Linked 6‑Deoxy‑l‑altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor

Synthesis of β‑(1→2)-Linked 6‑Deoxy‑l‑altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor

The β-(1→2)-linked 6-deoxy-l-altropyranose di- to pentasaccharides 2–5, relevant to the O-antigen of the infectious Yersinia enterocolitica O: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-be...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 82; no. 6; pp. 3062 - 3071
Main Authors: Shen, Zhengnan, Mobarak, Hani, Li, Wei, Widmalm, Göran, Yu, Biao
Format: Journal Article
Language:English
Published: United States American Chemical Society 17-03-2017
Subjects:
Organic Chemistry
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Summary:The β-(1→2)-linked 6-deoxy-l-altropyranose di- to pentasaccharides 2–5, relevant to the O-antigen of the infectious Yersinia enterocolitica O: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.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.7b00057