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Article Dans Une Revue European Journal of Organic Chemistry Année : 2022

Second Generation Synthesis of Modified Dinucleotide Analogues Featuring a Difluorophosphin(othio)yl Linkage

Résumé

Abstract Derivatives of 2’‐ O ‐4’‐ C ‐Ethylene‐bridged Nucleic Acid (ENA) monomer, a nucleoside used in the preparation of antisense modified oligonucleotides and featuring an alkyl group in position 7’, are stereoselectively produced in nine steps from commercially available 3‐ O ‐benzyl‐4‐(hydroxymethyl)‐1,2‐ O ‐isopropylidene‐alpha‐D‐ribofuranose. The synthesis relies on a sequence of reactions involving a Tebbe olefination, a key ring‐closing metathesis, and an enol ether reduction.
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Dates et versions

hal-03809902 , version 1 (11-10-2022)

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Citer

Prabhakar Sunchu, Sandrine Gaurrand, Émilie Lambert, Jérôme Guillemont, Leonid Beigelman, et al.. Second Generation Synthesis of Modified Dinucleotide Analogues Featuring a Difluorophosphin(othio)yl Linkage. European Journal of Organic Chemistry, 2022, 2022 (25), ⟨10.1002/ejoc.202200303⟩. ⟨hal-03809902⟩
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