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Chemical properties of 4,5-di(ethoxycarbonyl)-1,3-dioxolan-2-yl (DECDO) as a hydroxyl protecting group of the 2′-hydroxyl function in ribonucleosides

✍ Scribed by Boleslaw Karwowski; Kohji Seio; Mitsuo Sekine

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 524 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440208

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✦ Synopsis

Abstract

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We describe basic chemical properties of 4,5‐di(ethoxycarbonyl)‐1,3‐dioxolan‐2‐yl (DECDO) in view of its use as a protecting group for the 2′‐hydroxyl function of ribonucleosides. The DECDO group is found to be compatible with the DMTr strategy for the currently‐used oligonucleotide synthesis. Post‐synthetic treatment with ammonia results in the conversion of this protecting group into the 4,5‐dicarbamoyl‐1,3‐dioxolan‐2‐yl (DCBDO) group which is unexpectedly more stable in aqueous acidic solution.

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✍ Boleslaw Karwowski; Kohji Seio; Mitsuo Sekine 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 41 KB 👁 1 views