In this work, we have developed a simple synthetic approach using EtN·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--triflate-β-ᴅ-talopyranose using EtN·3HF or in situ generated EtN·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.
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| http://dx.doi.org/10.3762/bjoc.16.237 | DOI Listing |
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