Triethylamine → N-(9-((2R,4S,5R)-5-((Tert-butyldimethylsilyloxy)methyl)-4-hydroxytetrahydrofuran-2-YL)-9H-purin-6-YL)benzamide

Participants

Reaction Steps

N6 -Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine (Compound 5, Table I) was prepared by a procedure similar to that used to prepare the 5'-O-tertbutyldimethylsilylthymidine, as described in Example 1, except that N6 -benzoyl-2'-deoxyadenosine (10 g, 26.9 mmole), 4-N,N-dimethylaminopyridine (0.86 g, 7.0 mmole), triethylamine (3.6 g, 4.96 ml, 35.4 mmole) and tert-butyldimethylchlorosilane (5.33 g, 35.4 mmole) were dissolved in 100 ml dry N,N-dimethylformamide. The reaction was allowed to stir for 2 hours before being worked up as described in Example 1. Chromatography was performed using dichloromethane/ethanol (20/1) as eluent to yield 9.6 g N6 -benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxyadenosine as a white foam (73% yield).

Provenance & Evidence