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Keywords = nocardicin

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Article
Application of the N-Dibenzyl Protective Group in the Preparation of β-Lactam Pseudopeptides
by Rok Frlan, Martina Hrast and Stanislav Gobec
Molecules 2019, 24(7), 1261; https://doi.org/10.3390/molecules24071261 - 1 Apr 2019
Cited by 2 | Viewed by 5386
Abstract
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 [...] Read more.
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. Full article
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