(±)-6,7-丙酮缩二醇-3-酮-庚酸乙酯合成研究

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

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,1HNMR,13CNMR和MS光谱表征.

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 synthesized 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.