-transparent.png){kind=logo}
It is reported that the diisobutylaluminum hydride (DIBALH) reduction of inosine and adenosine derivatives (1a and 1d) causes cleavage of the ribose moiety to give the corresponding 9-ribitylhypoxanthine (2a) and 9-ribityladenine (2d), respectively. The substitution effect of purine nucleosides on the reduction was investigated. O6-alkylinosine derivatives (1b and 1c) were reduced in good yields like 1a. Introduction of methyl group into the N6-position of adenosine (1d), however, greatly reduced the reactivity toward DIBALH. The reduction of 7-deazainosine (3a) and 7-deazaadenosine (3b) hardly proceeded. These results suggest that oxygenophilicity of aluminum atom facilitates coordination of DIBALH to the 7-ring nitrogen atom and accelerate a cleavage of the ribose.
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
January 1984,
Advances in experimental medicine and biology,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
October 1967,
Die Naturwissenschaften,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
April 1974,
Nucleic acids research,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
April 1964,
Biochemistry,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
September 1959,
The Journal of clinical investigation,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
September 2018,
Organic letters,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
April 1977,
European journal of biochemistry,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
January 1978,
Verhandlungen der Deutschen Gesellschaft fur Innere Medizin,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
December 1978,
Tropenmedizin und Parasitologie,
K Hirota, and
Y Monguchi, and
M Sako, and
Y Kitade
April 2009,
The journal of physical chemistry. B,
