4.6 Article

Stereoselective synthesis of beta-rhamnopyranosides via gold(I)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 14, Issue 5, Pages 1536-1539

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob02551f

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Funding

  1. Ministry of Sciences and Technology of China [2012ZX09502-002]
  2. Natural Science Foundation of China [21432012, 21372253]

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Stereoselective beta-rhamnopyranosylation remains a challenge, due to the unfavorable anomeric effect and steric hindrance of the C2-substituent; herein, this challenge is addressed with a gold(I)-catalyzed S(N)2-like glycosylation protocol employing alpha-rhamnopyranosyl 2-alkynyl-4-nitro-benzoates as donors.

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