Polymer-supported Stereoselective Synthesis of Benzoxazino[4,3-b][1,2,5]thiadiazepinone-6,6-dioxides
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F17%3A73583781" target="_blank" >RIV/61989592:15110/17:73583781 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/17:73583781
Result on the web
<a href="http://pubs.acs.org/doi/10.1021/acscombsci.7b00115" target="_blank" >http://pubs.acs.org/doi/10.1021/acscombsci.7b00115</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acscombsci.7b00115" target="_blank" >10.1021/acscombsci.7b00115</a>
Alternative languages
Result language
angličtina
Original language name
Polymer-supported Stereoselective Synthesis of Benzoxazino[4,3-b][1,2,5]thiadiazepinone-6,6-dioxides
Original language description
Herein, we report the stereoselective synthesis of trisubstituted benzoxazino[4,3-b][1,2,5]thiadiazepinone 6,6-dioxides from polymer-supported Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH. After the solid-phase synthesis of N-alkylated-N-sulfonylated intermediates using various 2-nitrobenzenesulfonyl chlorides and bromoketones, the target compounds were obtained via trifluoroacetic acid (TFA)-mediated cleavage from the resin followed by cyclization of the diazepinone scaffold. Except for the threonine-based intermediates, the inclusion of triethylsilane (TES) in the cleavage cocktail yielded a specific configuration of the newly formed C3 chiral center. The final cyclization resulted in minor or no inversion of the C12a stereocenter configuration.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
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)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Combinatorial Science
ISSN
2156-8952
e-ISSN
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Volume of the periodical
19
Issue of the periodical within the volume
10
Country of publishing house
US - UNITED STATES
Number of pages
5
Pages from-to
670-674
UT code for WoS article
000412864700008
EID of the result in the Scopus database
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