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Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

✍ Scribed by Satoshi Obika; Jyun-ichi Andoh; Mayumi Onoda; Osamu Nakagawa; Akiko Hiroto; Tomomi Sugimoto; Takeshi Imanishi

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 190 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)01279-6

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✦ Synopsis

A novel bridged nucleic acid monomer, 3%-amino-3%-deoxy-5-methyl-3%-N,4%-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A 1 H NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3%-amino-3%,4%-BNA, was restricted to S-type conformation.

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