5'-DMT-RIBO ADENOSINE (N-BZ)

Uses

Synthesis

40615-36-9

4546-55-8

129666-75-7

The general procedure for the synthesis of the target compound (CAS: 129666-75-7) from 4,4'-dimethoxytrityl chloride (DMTrCl) and N6-benzoyl adenosine was as follows: to a pyridine solution (100 g, 269.3 mmol, 0.5 mmol) containing N-(9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl) at 0 °C, N-(9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl )-benzamide (100 g, 269.3 mmol) to a pyridine solution (500 mL) was added DMAP (1.64 g, 13.46 mmol, 0.05 equiv) and DMTrCl (100.4 g, 296.2 mmol, 1.1 equiv) in sequence. The reaction mixture was stirred at room temperature for 16 h. Upon completion of the reaction, the reaction was quenched by addition of methanol (500 mL). Volatiles were removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (elution gradient: 1/1 petroleum ether/ethyl acetate to 100% ethyl acetate) to afford N-(9-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzene Formamide, as a white foamy solid (150 g, 223 mmol, 83% yield).

References