CAJ | 학술논문

以剑麻皂甙元为原料,经氧化降解得到了手性目标化合物.再与溴化氢/无水乙醇反应,以86%的收率得到(R)-4-溴-3-甲基丁酸乙酯;当目标化合物与苄溴/氢氧化钠反应时,可选择性地分别以91%和90%的收率得到(R)-4-苄氧基-3-甲基丁酸和(R)-4-苄氧基-3-甲基丁酸苄酯.合成产物的结构采用IR、~1HNMR和MS等确认.它们不仅为药物和生物活性天然化合物的合成提供了新的合成中间体,也为它们的新合成途径设计提供了机遇.
이검마조대원위원료,경양화강해득도료수성목표화합물.재여추화경/무수을순반응,이86%적수솔득도(R)-4-추-3-갑기정산을지;당목표화합물여변추/경양화납반응시,가선택성지분별이91%화90%적수솔득도(R)-4-변양기-3-갑기정산화(R)-4-변양기-3-갑기정산변지.합성산물적결구채용IR、~1HNMR화MS등학인.타문불부위약물화생물활성천연화합물적합성제공료신적합성중간체,야위타문적신합성도경설계제공료궤우.
(R)-β-Methyl-γ-butyrolactone,a chiral building block,was obtained from the waste resulted from the degradation of tigogenin.Ethyl (R)-4-bromo-3-methyl butyrate was synthesized via the reaction of (R)-β-methyl-γ-butyrolactone with HBr/EtOH in 86% yield,and the compound were chemo-selectively converted into (R)-4-benzyloxy-3-methylbutanoic acid and benzyl (R)-4-benzyloxy-3-methyl butyrate by the reaction with BnBr/NaOH in 91% and 90% yields,respectively.The structures of the products were confirmed by IR,~1HNMR and MS.These chiral reagents not only provide the important intermediates for the synthesis of chiral drugs and the optically active natural compounds,they also offer the opportunities for design of new synthetic routes.