FACILE CONVERSION OF N6-BENZOYLADENOSINES INTO 5'-CHLORO-5'-DEOXY-8-HYDROXYADENOSINES BY A REACTION WITH CUPRIC CHLORIDE : A PROMINENT SUBSTITUENT EFFECT OF THE N6-BENZOYL GROUP

Yukio KITADE; Ryuji NAKANISHI; Magoichi SAKO; Kosaku HIROTA; Yoshifumi MAKI

doi:10.1248/cpb.39.1902

FACILE CONVERSION OF N⁶-BENZOYLADENOSINES INTO 5'-CHLORO-5'-DEOXY-8-HYDROXYADENOSINES BY A REACTION WITH CUPRIC CHLORIDE : A PROMINENT SUBSTITUENT EFFECT OF THE N⁶-BENZOYL GROUP

Yukio KITADE, Ryuji NAKANISHI, Magoichi SAKO, Kosaku HIROTA, Yoshifumi MAKI

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Keywords: adenosine derivative, 5'-O, 8-cycloadenosine, oxidative cyclization, cupric chloride, imino-ether bond cleavage, 5'-chloro-8-hydoxyadenosine, N⁶-substituent effect

JOURNAL FREE ACCESS

1991 Volume 39 Issue 7 Pages 1902-1904

DOI https://doi.org/10.1248/cpb.39.1902

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Abstract

Facile conversion of N⁶-benzoyl-2', 3'-O-isopropylideneadenosine (1) into N⁶-benzoyl-5'-chloro-5'-deoxy-8-hydroxy-2', 3'-O-isopropylideneadenosine (3) by a reaction with cupric chloride in acetonitrile provides a new method for the chemical modification of adenosines. This reflects the prominent substitutent effect of N⁶-benzoyl group on the chemical reactivity of adenosines.

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