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. Author manuscript; available in PMC: 2011 Jun 24.
Published in final edited form as: Chem Biol. 2005 Feb;12(2):237–247. doi: 10.1016/j.chembiol.2004.12.010

Figure 3. Synthetic Routes to Various Mono-and Disubstituted Adenosine-5′-Uronamide.

Figure 3

Derivatives (A) Synthesis of adenosine-5′-uronamide analogs 1 and 8–10.

(B) Synthesis of N6-(2-methylbenzyl)adeno-sine-5′-uronamide analogs 12–15. Reagents: (i) CrO3, AcOH, 18%; (ii) TMSCHN2, MeOH, 88%; (iii) RNH2, DMF, 60°C; (iv) 1N HCl MeOH-H2O (1:1) 55°C, 2 d; (v) RP-SiO2 C18, for 7, Amberlite CG-50, for 11 and 12–15; (vi) Boc-NH(CH2)nNH2, iPr2NEt, DMF, 60°C, 54%–97%; (vii) Amberlite CG-50, 13%–67%; (viii) 2-MeBnBr; (ix) ethylamine or ethanol-amine, MeOH, heat, Dimroth rearrangement and aminolysis of ester.