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

Submitting author affiliation:
Institute of Chemical Process Fundamentals of the CAS, v. v. i., Praha, Czech Republic

Beilstein Arch. 2021, 202110.

Published 11 Feb 2021

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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 phenyltrimethylsilyl sulfide. Nucleophilic deoxyfluorination at C4 and C6 by reaction with DAST, thioglycoside hydrolysis and azide/acetamide transformation completed the synthesis.

Keywords: Fluorinated carbohydrates; deoxyfluorination; amino sugars; thioglycosides; hexosamine hemiacetals

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Hamala, V.; Červenková Šťastná, L.; Kurfiřt, M.; Cuřínová, P.; Dračínský, M.; Karban, J. Beilstein Arch. 2021, 202110. doi:10.3762/bxiv.2021.10.v1

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