Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide thiodonors.
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F21%3A00539717" target="_blank" >RIV/67985858:_____/21:00539717 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/21:00539717
Result on the web
<a href="https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-85.pdf" target="_blank" >https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-85.pdf</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3762/bjoc.17.85" target="_blank" >10.3762/bjoc.17.85</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide thiodonors.
Original language description
Multiple fluorination of glycostructures has emerged as an attractive way of modulating their protein affinity, metabolic stability, and lipophilicity. Here we described the synthesis of a series of mono-, di- and trifluorinated N-acetyl-D-glucosamine and D-galactosamine analogs. The key intermediates were the corresponding multiply fluorinated glucosazide and galactosazide thiodonors prepared from deoxyfluorinated 1,6-anhydro-2-azido-β-D-hexopyranose precursors by ring-opening reaction with phenyl trimethylsilyl sulfide. Nucleophilic deoxyfluorination at C4 and C6 by reaction with DAST, thioglycoside hydrolysis and azide/acetamide transformation completed the synthesis.
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)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Beilstein Journal of Organic Chemistry
ISSN
1860-5397
e-ISSN
1860-5397
Volume of the periodical
17
Issue of the periodical within the volume
MAY 11
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
1086-1095
UT code for WoS article
000651417700001
EID of the result in the Scopus database
2-s2.0-85106378865