CAJ | 학술논문

以N-Boc-（4R）-羟基-（L）-脯氨酸甲酯为原料，通过威廉逊醚化法，再去Boc保护进行合成（4R）-苄氧基-（2S）-脯氨酸的过程中，发现以NaH为碱性试剂时，其2-位的手性碳可发生部分消旋化；致使在合成（4R）-苄氧基-（2S）-脯氨酸的同时，可一锅法得到其非对映异构体（4R）-苄氧基-（2R）-脯氨酸。所得产物的结构分别通过1 H NMR、13 C NMR、HRMS、红外光谱、比旋光度和熔点等进行了确定。
이N-Boc-（4R）-간기-（L）-포안산갑지위원료，통과위렴손미화법，재거Boc보호진행합성（4R）-변양기-（2S）-포안산적과정중，발현이NaH위감성시제시，기2-위적수성탄가발생부분소선화；치사재합성（4R）-변양기-（2S）-포안산적동시，가일과법득도기비대영이구체（4R）-변양기-（2R）-포안산。소득산물적결구분별통과1 H NMR、13 C NMR、HRMS、홍외광보、비선광도화용점등진행료학정。
In the process of the synthesis of (4R)-Benzyloxy-(2S)-proline from N-Boc-(4R)-Hydroxy-(L)-Proline methyl ester by Williamson reaction and after removing the BOC group,it was found that the part racemization of the chiral carbon atom C-2 could occur in case of NaH used as a basic reagent, resulting in simultaneous formation of (4R )-Benzyloxy-(2S )-proline and diastereoisomer (4R )-Benzyloxy-(2R)-proline in one pot.The target compounds are characterized by 1 H NMR,1 3 C NMR, HRMS,IR,specific rotation and melting point.Based on this research,a simple,effective and reliable method for the synthesis of D-proline derivatives could be constructed.