Synthesis of 7'‐Substituted 2'‐O‐4'‐C‐Ethylene Bridged Nucleic Acid (ENA)‐Thymidine Monomers.

Autor:	Sunchu, Prabhakar, Gaurrand, Sandrine, Lambert, Émilie, Guillemont, Jérôme, Beigelman, Leonid, Brioche, Julien, Piettre, Serge R.
Předmět:	MONOMERS ALKYL group ENOL ethers METATHESIS reactions NUCLEIC acids OLIGONUCLEOTIDES HYDROXYMETHYL compounds NUCLEOSIDE derivatives
Zdroj:	European Journal of Organic Chemistry; 1/2/2024, Vol. 27 Issue 1, p1-6, 6p
Abstrakt:	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. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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