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Towards novel amide-modified oligonucleotides: asymmetric synthesis of 5′-(S)-methyl-3′-carboxymethylene-3′-deoxythymidine

✍ Scribed by Sebastian Wendeborn; Hannes Nussbaumer; Frédéric Robert; Mario Jörg; Johannes Paul Pachlatko

Book ID: 104251469
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 197 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01053-5

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✦ Synopsis

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 mediated cleavage of a [3.2.1] oxabicyclic lactone.

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