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First synthesis of 2',3'-epimino-carbocyclic nucleosides. 2003

Minoru Ishikura, and Atsushi Murakami, and Nobuya Katagiri
Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan. ishikura@hoku-iryo-u.ac.jp

The preparation of 2',3'-epimino-carbocyclic analogues of adenosine is reported. The reaction of p-tosyl azide with N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1a) provided aziridine-fused ABH (2), which was converted to 2',3'-epimino-carbocyclic nucleosides (11).

UI MeSH Term Description Entries
D007769 Lactams Cyclic AMIDES formed from aminocarboxylic acids by the elimination of water. Lactims are the enol forms of lactams. Lactam,Lactim,Lactims
D009705 Nucleosides Purine or pyrimidine bases attached to a ribose or deoxyribose. (From King & Stansfield, A Dictionary of Genetics, 4th ed) Nucleoside,Nucleoside Analog,Nucleoside Analogs,Analog, Nucleoside,Analogs, Nucleoside
D000241 Adenosine A nucleoside that is composed of ADENINE and D-RIBOSE. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. Adenocard,Adenoscan
D001386 Azides Organic or inorganic compounds that contain the -N3 group. Azide

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