6-(2-Alkylimidazol-1-yl)purines undergo regiospecific glycosylation at N9.
[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).
Zhong
Minghong
M
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Nowak
Ireneusz
I
Robins
Morris J
MJ
D006031:Glycosylation; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D011687:Purines / Q000737:chemistry*; D013237:Stereoisomerism
D007093:Imidazoles; D011687:Purines