Ontology highlight
ABSTRACT:
SUBMITTER: Laine D
PROVIDER: S-EPMC7705882 | biostudies-literature | 2020
REPOSITORIES: biostudies-literature
Lainé Danny D Denavit Vincent V Lessard Olivier O Carrier Laurie L Fecteau Charles-Émile CÉ Johnson Paul A PA Giguère Denis D
Beilstein journal of organic chemistry 20201125
In this work, we have developed a simple synthetic approach using Et<sub>3</sub>N·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-<i>O</i>-triflate-β-ᴅ-talopyranose using Et<sub>3</sub>N·3HF or in situ generated Et<sub>3</sub>N·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 contin ...[more]