6-(2-Alkylimidazol-1-yl)purines undergo regiospecific glycosylation at N9
Minghong Zhong1, Ireneusz Nowak, Morris J Robins
1Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Abstract:
[reaction: see text] Regioselective control of glycosylation of purines at N9 (versus N7) has been a continuing challenge. We now report Lewis acid catalyzed regiospecific glycosylations of 6-(2-alkylimidazol-1-yl)purines at N9. The 6-(2-alkyl)imidazole moiety also functions as a versatile leaving group that can be replaced by nucleophiles (S(N)Ar) and aryl groups (Suzuki cross-coupling).
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