Diazabicyclo[5.4.0]undec-7-ene → 8-(((3R,3aR,6R,6aS)-6-((tert-butyldimethyl-silyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine

Participants

Reaction Steps

To a stirring solution of 2-chloro-8-(methylsulfonyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine (182 mgs, 0.50 mmol) and (3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (131.0 mg, 0.50 mmol) in anhydrous DMF (4.1 mL) was added diazabicyclo[5.4.0]undec-7-ene (DBU, 0.11 mL, 0.75 mmol). The reaction was stirred under N2 at RT for 16 h and then evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 24 g silica RediSep Rf® Gold column and employing a 0-75% EtOAc/hexane gradient afforded the title compound. LC-MS: calculated for C23H39ClN4O5Si2 542.21 observed m/e: 543.53 (M+H)+ (Rt 1.54/2.0 min)

Provenance & Evidence