Solid-Phase Synthesis of gamma-Lactone and 1,2-Oxazine Derivatives and Their Efficient Chiral Analysis

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F16%3A10335061" target="_blank" >RIV/00216208:11160/16:10335061 - isvavai.cz</a>

Result on the web

<a href="http://dx.plos.org/10.1371/journal.pone.0166558" target="_blank" >http://dx.plos.org/10.1371/journal.pone.0166558</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1371/journal.pone.0166558" target="_blank" >10.1371/journal.pone.0166558</a>

Result language

angličtina

Original language name

Solid-Phase Synthesis of gamma-Lactone and 1,2-Oxazine Derivatives and Their Efficient Chiral Analysis

Original language description

Derivatives of 3-methyl-3,6-dihydro-2H-1,2-oxazine-6-carboxylic acid prepared by regioselective hetero Diels-Alder reaction of arylnitroso compounds with sorbic acid were used for solid-phase synthesis of a library of derivatives that included modification of carboxylic group, dihydroxylation of double bond and cleavage of N-O bond. Derivatives of 2,3,4-trihydroxyhexanoic acid obtained from 3,6-dihydro-2H-1,2-oxazines after double bond dihydroxylation and N-O cleavage were used for simple and stereoselective formation of chiral lactones derived from 3,4-dihydroxydihydrofuran-2(3H)-one. The final compounds obtained as a mixture of stereoisomers were analyzed with use of chiral HPLC and SFC. HPLC analyses were not successful for all derivatives or required lengthy chromatography. On the other hand SFC afforded much shorter analyses and was effective for all studied derivatives. The method of synthesis and analysis is thus suitable for future study of stereoselective synthesis of lactones and other derivatives from single oxazine derivatives and application of high-throughput synthesis on solid-support and combinatorial chemistry.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

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Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

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

Name of the periodical

PLoS ONE

ISSN

1932-6203

e-ISSN

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Volume of the periodical

11

Issue of the periodical within the volume

11

Country of publishing house

US - UNITED STATES

Number of pages

23

Pages from-to

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UT code for WoS article

000389472400031

EID of the result in the Scopus database

2-s2.0-84999027824