AI Article Synopsis
- This text discusses methods for synthesizing (S)-cEt-BNA, an important component in antisense oligonucleotides, starting from 5-methyluridine.
- The shorter synthesis method utilizes a nine-step linear process, resulting in an O-protected (S)-cEt-BNA with a specific dioxabicycloheptane structure and a low overall yield of 7%.
- Additionally, it mentions that a competing reaction occurred during the process, leading to the formation of a bicyclic oxetane instead.
Article Abstract
Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.1]dioxabicycloheptane core in 7% overall yield. A competing reaction in an intramolecular cyclization of a tosylate led to a bicyclic oxetane.
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| http://dx.doi.org/10.1021/jo502320y | DOI Listing |
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Alternative syntheses of (S)-cEt-BNA: a key constrained nucleoside component of bioactive antisense gapmer sequences.
J Org Chem
December 2014
Department of Chemistry, Université de Montréal, Montréal, Québec H3C 3J7, Canada.
Approaches to the synthesis of the constrained 5-methyluracil nucleoside (S)-cEt-BNA, a key "gapmer" unit in a number of biologically relevant antisense oligonucleotides, are described using 5-methyluridine as starting material. In the shorter synthesis, a nine-step linear sequence afforded a O-protected (S)-cEt-BNA consisting of a [2.2.
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