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Communication | Special issue | Vol 42, No. 1, 1996, pp.57-63
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S19
Synthesis of N6,2’,3’,5’-Tetrabenzoyl-β-D-adenosine Catalyzed by Metal Iodides

Masashi Nagai, Takafumi Matsutani, and Teruaki Mukaiyama

*Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan

Abstract

N-Glycosylation of N6-benzoyl-N6,N6-bis(trimethylsilyl)adenine with methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate was effectively promoted by several metal iodides and a desired coupling product, N6, 2’, 3’,5’-tetrabenzoyl-β-D-adenosine (3), was obtained in high yield when SbI3 or TeI4 was used as a catalyst. In the case of using SnI2 as a catalyst, nearly equal amounts of 3 and 2’,3’,5‘-tribenzoyl-β-D-adenosine (4), a N6-debenzoylated product of 3, were produced in acetonitrile whereas 3 was obtained as a major product in other nitrile solvents.