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%2F60461373%3A22310%2F20%3A43923766" target="_blank" >RIV/60461373:22310/20:43923766 - isvavai.cz</a>
Alternative codes found
RIV/67985858:_____/20:00525445 RIV/61388963:_____/20:00525445 RIV/60461373:22810/20:43923766
Result on the web
<a href="https://pubs.rsc.org/en/content/articlepdf/2020/ob/d0ob01065k" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2020/ob/d0ob01065k</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 thiodonors endowed 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 moiety abundant 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. This journal is © The Royal Society of Chemistry.
Czech name
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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
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OECD FORD branch
10401 - Organic chemistry

Project
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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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