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Paper | Special issue | Vol 79, No. 1, 2009, pp.873-882
Published online, 4th December, 2008
DOI: 10.3987/COM-08-S(D)58
Synthesis of a Novel trans-3’,4’-BNA Monomer Bearing a 4,8-Dioxa-5-azabicyclo[5.3.0]decane Skeleton

Tetsuya Kodama, Kensaku Sugaya, Takeshi Baba, Takeshi Imanishi, and Satoshi Obika*

*Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamadaoka, Suita, Osaka 560-0871, Japan


A novel trans-3’,4’-BNA monomer, in which sugar conformation was restricted to S-type by a trans-fused 3-oxa-4-azapentylene bridge between C3’ and C4’ position, was designed and synthesized. The trans-fused 7-membered cyclic structure within a 4,8-dioxa-5-azabicyclo[5.3.0]decane skeleton was prepared by means of intramolecular substitution reaction using potassium carbonate as a base. We found that all of protecting groups (benzyl, benzyloxymethyl, and benzyloxycarbonyl group) were able to be removed smoothly by DDQ oxidation followed by boron trichloride treatment without cleavage of N-O linkage to afford the desired trans-3’,4’-BNA monomer.