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

  1. Vojtěch Hamala,
  2. Lucie Červenková ŠťastnáORCID Logo,
  3. Martin Kurfiřt,
  4. Petra Cuřínová,
  5. Martin DračínskýORCID Logo and
  6. Jindřich KarbanORCID Logo

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

Beilstein Arch. 2021, 202110. https://doi.org/10.3762/bxiv.2021.10.v1

Published 11 Feb 2021

  • Preprint

Abstract

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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