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Regioselective acylation of 2′- or 3′-hydroxyl group in salicin: Hemisynthesis of acylated salicins

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Abstract

Salicin-based phenolic glycosides(PGs) are important defensive substances against herbivore feeding and have good bioactivities. In this work, a novel approach for the synthesis of salicin-based PGs has been developed, by which PGs of 2′-O-acetylsalicin(5a), 3′-O-acetylsalicin(5b) and 3′-O-benzoylsalicin(5d) were hemisynthesized. The effects of acylation reagent, solvent and temperature on the regioselective acylation of 2′- or 3′-hydroxyl groups of salicin mediated by dibutyltin oxide were investigated. The optimal conditions under which the best regioselectivity reached for 5a–5d were discovered, respectively. Moreover, a tentative tin-oxygen coordination mechanism was put forward to explain the different regioselectivities shown under different conditions.

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Authors and Affiliations

  1. College of Science, Northwest A&F University, Yangling, 712100, P. R. China

    Chen Shao, Yuxin Pei & Zhichao Pei

  2. Department of Chemistry, KTH Royal Institute of Technology, Stockholm, S-10044, Sweden

    Anna-Karin Borg-Karlson

Authors
  1. Chen Shao
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  2. Yuxin Pei
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  3. Anna-Karin Borg-Karlson
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  4. Zhichao Pei
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Corresponding authors

Correspondence to Yuxin Pei or Zhichao Pei.

Additional information

Supported by the National Natural Science Foundation of China(No.31270861/C050204), the Agricultural Science and Technology Innovation Project of Shaanxi Province, China(No.2012 NKC01-12) and the Talent Start-up Fund of Northwest Sci-tech University of Agriculture and Forestry University, China.

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Shao, C., Pei, Y., Borg-Karlson, AK. et al. Regioselective acylation of 2′- or 3′-hydroxyl group in salicin: Hemisynthesis of acylated salicins. Chem. Res. Chin. Univ. 30, 774–777 (2014). https://doi.org/10.1007/s40242-014-4041-y

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  • DOI: https://doi.org/10.1007/s40242-014-4041-y

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