Regioselective Acylation of 2'-or 3'-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins

doi:10.1007/s40242-014-4041-y

Chemical Research in Chinese Universities ›› 2014, Vol. 30 ›› Issue (5): 774-777.doi: 10.1007/s40242-014-4041-y

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Regioselective Acylation of 2'-or 3'-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins

SHAO Chen¹, PEI Yuxin¹, BORG-KARLSON Anna-Karin², PEI Zhichao¹

1. College of Science, Northwest A&F University, Yangling 712100, P. R. China;
2. KTH Royal Institute of Technology, Department of Chemistry, Stockholm S-10044, Sweden

Received:2014-02-11 Revised:2014-04-08 Online:2014-10-01 Published:2014-05-12
Contact: PEI Yuxin, PEI Zhichao E-mail:peiyx@nwsuaf.edu.cn;peizc@nwafu.edu.cn
Supported by:
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

Abstract

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-5dwere discovered, respectively. Moreover, a tentative tin-oxygen coordination mechanism was put forward to explain the different regioselectivities shown under different conditions.

Key words: Regioselective acylation, Salicin, Phenolic glycoside, Tin-oxygen coordination, Hemisynthesis

SHAO Chen, PEI Yuxin, BORG-KARLSON Anna-Karin, PEI Zhichao. Regioselective Acylation of 2'-or 3'-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins[J]. Chemical Research in Chinese Universities, 2014, 30(5): 774-777.

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Regioselective Acylation of 2'-or 3'-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins

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