| Regioselective Acylation of 2＇- or 3＇-Hydroxyl Group in Salicin： Hemisynthesis of Acylated Salicins |
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| 作者姓名： | SHAO Chen ;PEI Yuxin ;BORG-KARLSON ;Anna-Karin ;PEI Zhichao |
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| 作者单位： | [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 |
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| 基金项目： | 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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| 摘 要： | 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-acetylsaliein（5a）, 3＇-O-acetylsalicin（gb） and 3＇-O-benzoylsalicin（Sd） 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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| 关 键 词： | 区域选择性 酰化试剂 水杨苷 羟基 二丁基锡 防御物质 生物活性 最佳条件 |
| 收稿时间： | 2014-02-11 |
Regioselective Acylation of 2'-or 3'-Hydroxyl Group in Salicin: Hemisynthesis of Acylated Salicins |
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| 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 University,2014,30(5):774-777. |
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| Authors: | SHAO Chen PEI Yuxin BORG-KARLSON Anna-Karin PEI Zhichao |
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| Institution: | 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 |
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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-5dwere 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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| Keywords: | Regioselective acylation Salicin Phenolic glycoside Tin-oxygen coordination Hemisynthesis |
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