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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (04): 462-464. 上一篇    下一篇

研究论文

(±)-6,7-丙酮缩二醇-3-酮-庚酸乙酯合成研究

杨华，王孝伟，陈艳丽，张志丽，刘俊义*   

  1. (北京大学药学院化学生物学系 北京 100083)
  • 收稿日期:2005-05-05 修回日期:2005-10-21 发布日期:2006-03-31
  • 通讯作者: 刘俊义

Study on Synthesis Ethyl 3-Oxo-(±)-6,7-di-O-isopropylidene-6,7-di-hydroxyheptanoate

YANG Hua,WANG Xiao-Wei,CHEN Yan-Li,ZHANG Zhi-Li,LIU Jun-Yi*   

  1. (Department of Chemical Biology, School of Pharmaceutical Sciences, Peking Univer-sity, Beijing 100083)
  • Received:2005-05-05 Revised:2005-10-21 Published:2006-03-31
  • Contact: LIU Jun-Yi

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用对甲苯磺酸-2,3-丙酮缩甘油酯(2)与乙酰乙酸乙酯盐、碳酸二乙酯反应, 制备β-酮酯类衍生物1. 以(±)-1,2-丙酮缩甘油为起始物, 经对甲苯磺酰化、亲核取代、脱羧等反应, 方便、高产率地合成了6,7-丙酮缩二醇-3-酮-庚酸乙酯(1). 试图通过对甲苯磺酸-2,3-丙酮缩甘油酯(2)和乙酰乙酸乙酯双阴离子反应制备6,7-丙酮缩二醇-3-酮-庚酸乙酯(1)未获成功. 所合成的化合物经元素分析, IR, 1H NMR, 13C NMR和MS光谱表征.

关键词: β-酮酯, 6,7-丙酮缩二醇-3-酮-庚酸乙酯, 乙酰乙酸乙酯盐, 合成

A new approach to synthesis of β-ketoester derivatives was reported. As a key starting material in the synthesis of neuroprotective agents and HIV-1 RT inhibitors, Ethyl 3-oxo-(±)-6,7-di-O-isopropylidene-6,7-dihydroxyheptanoate (1) was conveniently synthe-sized from (±)-solketal and ethyl acetoacetate sodium salt through four steps of reactions. An attempt to prepare the target compound 1 by the reaction of tosylate solketal 2 and dianion of ethyl acetoacetate was unsuccessful. The structure of all compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR and MS spectra.

Key words: -ketoester, synthesis, ethyl 3-oxo-(±)-6,7-di-O-isopropylidene-6,7-dihydroxyheptanoate, ethyl acetoacetate sodium salt,