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Asymmetric synthesis of 3′-carbomethoxymethyl 3′-deoxythymidine via radical cyclization

✍ Scribed by Jean-Francois Lavallée; George Just

Book ID
103401381
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
256 KB
Volume
32
Category
Article
ISSN
0040-4039

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Towards novel amide-modified oligonucleotides: asymmetric synthesis of 5′-(S)-methyl-3′-carboxymethylene-3′-deoxythymidine
✍ Sebastian Wendeborn; Hannes Nussbaumer; Frédéric Robert; Mario Jörg; Johannes Pa 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 197 KB

The synthesis of novel 5%-(S)-methyl-3%-carboxymethylene-3%-deoxythymidine is reported. Key steps involve diastereoselective lactonization, enantioselective enzymatic ester hydrolysis and diastereoselective glycosidation of a key intermediate with thymine with 100% b-selectivity via Lewis acid media