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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

<a href="/cs/project/EE2.3.20.0009" target="_blank" >EE2.3.20.0009: Kombinatoriální chemie ve výzkumu i vzdělávání</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

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Svazek periodika

38

Číslo periodika v rámci svazku

2014

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

5491-5499

Kód UT WoS článku

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EID výsledku v databázi Scopus

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