摘要
以2-溴丙酸和N-叔丁氧羰基-O-苄基-L-丝氨酸为起始试剂首先制得N-(2-溴丙基)-O-苄基-L-丝氨酸(BPBS),在N,N-二甲基甲酰胺(DMF)/三乙胺(Et3N)溶剂中80℃经9h后BPBS发生分子内环化反应生成(3S,6S)-3-苄氧甲基-6-甲基-吗啉-2,5-二酮[(3S,6S)-BMMD]及(3S,6R)-BMMD共存体,产率70%.将所制得的共存体以乙酸乙酯为重结晶溶剂,采用微分重结晶法,经4次"溶解-部分重结晶"操作循环制得两种纯光学构型的(3S,6S)-BMMD和(3S,6R)-BMMD.将两种光学纯双手性中心的BMMD分别溶于乙酸乙酯,室温下培养得(3S,6S)-BMMD和(3S,6R)-BMMD的单晶体,以X射线衍射法测定上述两种BMMD的分子结构.
N-（2-Bromopropionyl）-O-benzyl-L-serine （BPBS） was prepared using 2-bromopropionic acid and N-Boc-O-Bzl-L-serine as the starting reagents. BPBS underwent the intra-molecular ring-closing reac- tion in DMF/Et3N solvent at 80 ℃ for 9 h forming a mixture of two non-enantiomers, i.e. （3S,6S）-benzyloxymethyl-6-methyl-morpholine-2,5-dione [（3S,6S）-BMMD] and （3S,6R）-BMMD with a yield of 70%. Two optically pure enantiomers of BMMD, i.e. （3S,6S）-BMMD and （3S,6R）-BMMD were obtained via 4 operation circles of ＂solution-partial recrystallization＂ by means of a differential recrystallization method using ethyl acetate as a solvent. The single crystals of the two isomers of BMMD were grown from ethyl acetate at room temperature. The fine molecular structures of the two isomers were determined by X-ray diffraction analysis of the single crystals.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2009年第5期737-742,共6页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.20474030)资助项目
