Polymer-supported stereoselective synthesis of tetrahydro-2H-oxazolopyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-derivatized dipeptides via eastbound iminiums

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F13%3A33147702" target="_blank" >RIV/61989592:15310/13:33147702 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/co3001567" target="_blank" >http://dx.doi.org/10.1021/co3001567</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/co3001567" target="_blank" >10.1021/co3001567</a>

Result language
angličtina
Original language name
Polymer-supported stereoselective synthesis of tetrahydro-2H-oxazolopyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-derivatized dipeptides via eastbound iminiums
Original language description
Polymer-supported N-(2-oxo-ethyl)-derivatized Ser/Thr/Cys-containing dipeptides were synthesized and subjected to acid-mediated tandem N-acyliminium ion cyclization ? nucleophilic addition to yield tetrahydro-2H-oxazolo-pyrazin-5(3H)-ones. The reaction conditions and building-block combinations for stereoselective synthesis of the newly formed asymmetric carbon were developed. The synthesis was fully compatible with solid-phase peptide synthesis, and the products serve as conformationally constrained peptidomimetics. The traceless synthesis of bicycles is also reported as part of this work.
Czech name
—
Czech description
—

Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)