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Shen Z, Mobarak H, Li W, et al. Synthesis of β-(1→2)-Linked 6-Deoxy-l-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor. J Org Chem. 2017;82(6):3062-3071doi: 10.1021/acs.joc.7b00057.
Shen, Z., Mobarak, H., Li, W., Widmalm, G., & Yu, B. (2017). Synthesis of β-(1→2)-Linked 6-Deoxy-l-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor. The Journal of organic chemistry, 82(6), 3062-3071. https://doi.org/10.1021/acs.joc.7b00057
Shen, Zhengnan, et al. "Synthesis of β-(1→2)-Linked 6-Deoxy-l-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor." The Journal of organic chemistry vol. 82,6 (2017): 3062-3071. doi: https://doi.org/10.1021/acs.joc.7b00057
Shen Z, Mobarak H, Li W, Widmalm G, Yu B. Synthesis of β-(1→2)-Linked 6-Deoxy-l-altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor. J Org Chem. 2017 Mar 17;82(6):3062-3071. doi: 10.1021/acs.joc.7b00057. Epub 2017 Mar 02. PMID: 28230982.
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J Org Chem. 2017 Mar 17;82(6):3062-3071. doi: 10.1021/acs.joc.7b00057. Epub 2017 Mar 02.

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

The Journal of organic chemistry

Zhengnan Shen, Hani Mobarak, Wei Li, Göran Widmalm, Biao Yu

Affiliations

  1. School of Physical Science and Technology, ShanghaiTech University , 100 Haike Road, Shanghai 201210, China.
  2. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
  3. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University , S-106 91 Stockholm, Sweden.

PMID: 28230982 DOI: 10.1021/acs.joc.7b00057

Abstract

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 PPh

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