Solid-phase synthesis and analysis of 3,6-dihydro-2H-1,2-oxazines in their stereo- and regioisomer mixtures

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F14%3A33151977" target="_blank" >RIV/61989592:15110/14:33151977 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1039/C4NJ00974F" target="_blank" >http://dx.doi.org/10.1039/C4NJ00974F</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/C4NJ00974F" target="_blank" >10.1039/C4NJ00974F</a>

Result language
angličtina
Original language name
Solid-phase synthesis and analysis of 3,6-dihydro-2H-1,2-oxazines in their stereo- and regioisomer mixtures
Original language description
3,6-Dihydro-2H-1,2-oxazines were synthesised via solid-phase synthesis to afford mixtures of stereo- and regioisomers. The analytical conditions for the analysis of the isomer ratio suitable for checking of reaction conditions of possible stereoselective synthesis were developed with the use of HPLC including chiral stationary phases (CSPs) based on chiral polysaccharide derivatives immobilized on a silica support. It was found that those CSPs based on an amylose backbone were more efficient than those based on cellulose for the molecules investigated. Additionally, analytical samples without complete purification could be separated under the same conditions. The asymmetric induction causing the difference in the stereoisomer ratio was observed, when an oxazine ring was built up directly on a chiral moiety. A chiral aminoacid separated from the construction site by an achiral aromatic ring did not influence the ratio of stereoisomers. The analytical conditions developed were thus verified for use in the optimisation of the regio- and stereoselective synthesis of 3,6-dihydro-2H-1,2-oxazines. The conditions are suitable for solid-phase synthesis methodology often used in high throughput synthesis of biologically active compounds.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/EE2.3.20.0009" target="_blank" >EE2.3.20.0009: Combinatorial chemistry in research and education</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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