Use of remote acyl groups for stereoselective 1,2-cis-glycosylation with fluorinated glucosazide thiodonors.

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00525445" target="_blank" >RIV/61388963:_____/20:00525445 - isvavai.cz</a>
Alternative codes found
RIV/67985858:_____/20:00525445 RIV/60461373:22310/20:43923766 RIV/60461373:22810/20:43923766
Result on the web
<a href="http://hdl.handle.net/11104/0309994" target="_blank" >http://hdl.handle.net/11104/0309994</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d0ob01065k" target="_blank" >10.1039/d0ob01065k</a>

Result language
angličtina
Original language name
Use of remote acyl groups for stereoselective 1,2-cis-glycosylation with fluorinated glucosazide thiodonors.
Original language description
Fluorinated glycans are valuable probes for studying carbohydrate–protein interactions at the atomic level. Glucosamine is a ubiquitous component of glycans, and the stereoselective synthesis of α-linked fluorinated glucosamine is a challenge associated with the chemical synthesis of fluorinated glycans. We found that introducing a 6-O-acyl protecting group onto 3-fluoro and 4-fluoro glucosazide thiodonorsnendowed them with moderate α-selectivity in the glycosylation of carbohydrate acceptors, which was further improved by adjusting the acceptor reactivity via O-benzoylation. Excellent stereoselectivity was achieved for 3,6-di-O-acyl-4-fluoro analogues. The glycosylation of threonine-derived acceptors enabled the stereoselective synthesis of the protected fluorinated analogue of α-GlcNAc-O-Thr, a moietynabundant in cell-surface O-glycans of the protozoan parasite Trypanosoma cruzi. DFT calculations supported the involvement of transient cationic species which resulted from the stabilization of the oxocarbenium ion through O-6 acyl group participation.
Czech name
—
Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

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

Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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