Application of the N-Dibenzyl Protective Group in the Preparation of β-Lactam Pseudopeptides

Molecules

Martina Hrast¹  Stanislav Gobec¹  Rok Frlan¹ 

[1] The Chair of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000 Ljubljana, Slovenia;

关键词: β-lactams;    dibenzylamino;    Mitsunobu reaction;    nocardicin;    pseudopeptides;   

DOI  :  10.3390/molecules24071261

来源: DOAJ

【 摘 要 】

Despite the great importance of β-lactam antibiotics, there is still a limited number of synthetic approaches for the formation of β-lactam–containing dipeptides. In this study, we report upon the stereoselective preparation of β-lactam–containing pseudopeptides, where different reaction conditions and NH₂ protective groups were tested to obtain compounds that contain 3-amino-azetidin-2-one. We demonstrate that the protective group is essential for the outcome of the reaction. Successful implementation of dibenzyl-protected serine-containing dipeptides through the Mitsunobu reaction can provide the desired products at high yields and stereoselectivity.

【 授权许可】

Unknown