(-)-(2R_3S)-3-苯基-2_3-环氧丙酸甲酯；

-(2R,3S)-3-苯基-2，3-环氧丙酸甲酯的不对称合成

http://www.100md.com 《广东药学院学报》 2004年第2期

(-)-(2R,3S)-3-苯基-2,3-环氧丙酸甲酯；,,(-)-(2R,3S)-3-苯基-2，3-环氧丙酸甲酯；中间体；合成,1

     摘要以反式肉桂醇为原料，经Sharpless不对称环氧化，产生所需的两个手性碳(2S,3S)后，产物经氧化、酯化即得标题产物(-)-(2R,3S)-3-苯基-2，3-环氧丙酸甲酯(1)，三步总收率28.4%，所得产物的ee值>95%。

    关键词 (-)-(2R,3S)-3-苯基-2，3-环氧丙酸甲酯；中间体；合成

    Asymmetric synthesis of (-)-(2R,3S)-3-phenyl-2,3-

    epoxymethylpropionate

    LIN Hansen

    (Department of Medicinal Chemistry, Guangdong College of Pharmacy , Guangzhou, 510240)Abstract Asymmetric synthesis of (-)-(2R,3S)-3-phenyl-2,3-epoxymethylpropionate (1)by scheme 1 was described. Transcinnamyl alcohol was selected as a starting material,sharpless asymmetric epoxydation of tanscinnamyl alcohol can be carried out in the presence of tbutyl hydroperoxide,using (+)-diethyl tartrate as the asymmetric adjuvant, to produce two desired chiral centers(2S,3S). The title product (-)-(2R,3S)-3-phenyl-2,3-epoxymethylpropionate was obtained by successive oxidation and esterification with the overall of 28.4%(ee>95%).

    Key words (-)-(2R,3S)-3-Phenyl-2,3-epoxymethylpropionate; intermediate synthesis

    (-)-(2R,3S)-3-苯基-2 ......

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