Stereoselectivity in Glycosylation with Deoxofluorinated Glucosazide and Galactosazide Thiodonors
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00504616" target="_blank" >RIV/61388963:_____/19:00504616 - isvavai.cz</a>
Alternative codes found
RIV/67985858:_____/19:00504616
Result on the web
<a href="http://hdl.handle.net/11104/0296202" target="_blank" >http://hdl.handle.net/11104/0296202</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.9b00705" target="_blank" >10.1021/acs.joc.9b00705</a>
Alternative languages
Result language
angličtina
Original language name
Stereoselectivity in Glycosylation with Deoxofluorinated Glucosazide and Galactosazide Thiodonors
Original language description
Control of anomeric stereoselectivity in glycosylation with deoxofluorinated glycosyl donors is critical for assembly of fluorinated oligosaccharides. Here, we report the synthesis of benzylated 3-fluoro and 4-fluoro analogues of phenyl 1-thioglucosazide and galactosazide donors and evaluation of their stereoselectivity in glycosylation of a series of model carbohydrate acceptors using the Tf2O/Ph2SO promoter system. Low-temperature NMR revealed formation of covalent alpha-triflate and both anomers of oxosulfonium triflates under selected glycosylation conditions. This study demonstrates how the stereoselectivity depends on acceptor reactivity and glycosyl donor configuration. Reactive acceptors favor formation of 1,2- trans-beta-glycosides with both d- gluco and d- galacto donors, whereas poorly reactive acceptors favor formation of 1,2- cis-alpha-glycosides with d- galacto donors but are unselective with d- gluco donors.
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
<a href="/en/project/GA17-18203S" target="_blank" >GA17-18203S: Stereodirecting effects of deoxofluorination at C-3 and C-4 of 2-azido-2-deoxy-hexopyranosyl donors</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
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Volume of the periodical
84
Issue of the periodical within the volume
10
Country of publishing house
US - UNITED STATES
Number of pages
27
Pages from-to
6405-6431
UT code for WoS article
000468696400038
EID of the result in the Scopus database
2-s2.0-85065829028