1026468-15-4Relevant academic research and scientific papers
Simple, versatile and highly diastereoselective synthesis of 1,3,4-trisubstituted-2-oxopiperazine-containing peptidomimetic precursors
Franceschini, Nicolas,Sonnet, Pascal,Guillaume, Dominique
, p. 787 - 793 (2005)
The selective O-deprotection of (1'S)-4-(tert-butoxycarbonyl)-1-[1'- phenylmethyloxymethyl-2'-[(tert-butyldimethylsilyl)oxy]ethyl]-2-oxopiperazine furnished an enantiomerically pure alcohol whose regio- and diastereoselective C3-alkylation yielded either (3R)- or (3S)-1,3,4-trisubstituted-2- oxopiperazines in high diastereomeric purity. These derivatives were efficiently transformed into (1'A)- or (1'S)-peptide templates utilizable to prepare peptidomimetics. This method provides easy access to each 1,3,4-trisubstituted- 2-oxopiperazine diastereomer and facilitates, through the large choice of substituents at the 3-position together with the chemistry that can be performed on the NI substituent, the preparation of a large number of diastereomerically pure constrained peptidomimetics from a single precursor. The Royal Society of Chemistry 2005.
