Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide thiodonors.

0539717 - ÚCHP 2022 RIV DE eng J - Journal Article
Hamala, Vojtěch - Červenková Šťastná, Lucie - Kurfiřt, Martin - Cuřínová, Petra - Dračínský, Martin - Karban, Jindřich
Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide thiodonors.
Beilstein Journal of Organic Chemistry. Roč. 17, MAY 11 (2021), s. 1086-1095. ISSN 1860-5397. E-ISSN 1860-5397
R&D Projects: GA ČR(CZ) GA17-18203S; GA MŠMT(CZ) LTC20052
Grant - others:MEYS(XE) CA18103
Institutional support: RVO:67985858 ; RVO:61388963
Keywords : fluorinated carbohydrates * deoxyfluorination * amino sugars
OECD category: Organic chemistry; Physical chemistry (UOCHB-X)
Impact factor: 2.544, year: 2021
Method of publishing: Open access
https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-17-85.pdf

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.
Permanent Link: http://hdl.handle.net/11104/0318606