93527-55-0Relevant articles and documents
Application of the N-dibenzyl protective group in the preparation of β-lactam pseudopeptides
Frlan, Rok,Hrast, Martina,Gobec, Stanislav
, (2019/04/05)
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.
Improved enantioselective synthesis of protected (3S,4S)-4-amino-3,5- dihydroxypentanoic acid (ADPA)
Mei, Duo,Zhang, Wei,Li, Yingxia
experimental part, p. 1099 - 1105 (2010/04/29)
An improved enantioselective synthesis of protected (3S,4S)-4-amino-3,5- dihydroxypentanoic acid (ADPA) from L-serine has been developed. Enantioselectivity is improved by replacing the methyl ester with the tert-butyl ester and using neutral magnesium salt of esters to give β-keto ester.
Synthesis of Enterochelin
Rogers, Henry J.
, p. 3073 - 3076 (2007/10/03)
Enterochelin (enterobactin), the cyclic trilactone of N-(2,3-dihydroxybenzoyl)-L-serine 6, an important enterobacterial iron-transporting compound, has been synthesised from N,N-dibenzyl-L-serine 2 in four steps.The protected amino acid was oligomerised using N,N-dicyclohexylcarbodiimide in a high-dilution procedure yielding a mixture of di-, tri- and tetra-lactones.The trilactone 3b was deprotected by hydrogenolysis and the resultant amine 4 was acylated with 2,3-dibenzyloxybenzoyl chloride to yield hexa-O-benzylenterochelin 5.This upon hydrogenolysis gave enterochelin in moderate yield.
