Multi-step reaction with 14 steps
1: 79 percent / imidazole / dimethylformamide / 3 h / Ambient temperature
2: 75 percent / ethyl acetate / 1 h / Heating
3: 68 percent / 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / tetrahydrofuran / 2 h / Heating
4: 77 percent / m-Chloroperoxybenzoic acid / CHCl3 / 3.5 h
5: 99.7 percent / methanol
6: 1.) Et3N / 1.) DMF, 2.) DMF, r.t., 2h
7: 83 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / H2O; ethanol / 1.33 h / Heating
8: 67 percent / Aluminium amalgam / tetrahydrofuran; H2O / 26.5 h
9: 94 percent / 3M HCl / ethanol / 2.25 h
10: 93 percent / adenosine deaminase (EC.3.5.4.4) / H2O / 47.5 h / 37 °C / 0.5M disodium phosphate buffer, pH 7.5
12: 73 percent / H2O / acidified to pH 2
13: 1.) 1,1'-dicyclohexylcarbodiimide / 1.) water, tert-butyl alcohol, reflux, 4h, 2.) water, Dowex-1 1X2-200 (HCO3- form)
14: 1.) DMSO, r.t., 5d, 2.) ammonium hydrogen carbonate, water, DEAE Sephadex A-25 (HCO3- form)
With
1H-imidazole; 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; aluminium amalgam; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide;
adenosine deaminase (EC.3.5.4.4);
In
tetrahydrofuran; methanol; ethanol; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/P19910002467