Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

In this work, we have developed a simple synthetic approach using Et3N·3HF as an alternative to the DAST reagent. We controlled the stereochemistry of the nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-4-O-triflate-β-ᴅ-talopyranose using Et3N·3HF or in situ generated Et3N·1H...

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Bibliographic Details
Main Authors: Danny Lainé, Vincent Denavit, Olivier Lessard, Laurie Carrier, Charles-Émile Fecteau, Paul A. Johnson, Denis Giguère
Format: Article
Language:English
Published: Beilstein-Institut 2020-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
deoxyfluorination
et3n·3hf
fluorine effect
polyfluorinated carbohydrates
polyfluoroalditol analogues
Online Access:https://doi.org/10.3762/bjoc.16.237
Description
Summary:In this work, we have developed a simple synthetic approach using Et3N·3HF as an alternative to the DAST reagent. We controlled the stereochemistry of the nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-4-O-triflate-β-ᴅ-talopyranose using Et3N·3HF or in situ generated Et3N·1HF. The influence of the fluorine atom at C2 on reactivity at C4 could contribute to a new fluorine effect in nucleophilic substitution. Finally, with the continuous objective of synthesizing novel multi-vicinal fluorosugars, we prepared one difluorinated and one trifluorinated alditol analogue.
ISSN:1860-5397

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