Reaction #1951042

Reaction equation

tetrabutylammonium fluoride

acetic acid

Compound 22

5′-O-t-butyldimethylsilyl-2′,3′-dideoxy-4′-C-triethylsilylethynyl-2-fluoroadenosine

→

2′,3′-dideoxy-4′-C-ethynyl-2-fluoroadenosine

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Otherreaction mixture
2. 2
   Concentrationthe resultant mixture was concentrated under reduced pressure
3. 3
   OtherThe thus-obtained residue was purified by means of silica gel column chromatography (silica gel 15 ml, chloroform:methanol=40:1 to 20:1)

Procedure

Compound 22 (101 mg, 0.200 mmol) was dissolved in tetrahydrofuran (10 ml), and a solution of 1-M tetrabutylammonium fluoride in tetrahydrofuran (0.42 ml, 0.42 mmol) was added to the resultant solution, followed by stirring at room temperature for five minutes. After acetic acid (24 μl) was added to the resultant reaction mixture, the resultant mixture was concentrated under reduced pressure. The thus-obtained residue was purified by means of silica gel column chromatography (silica gel 15 ml, chloroform:methanol=40:1 to 20:1), to thereby yield compound 23 (53.0 mg, 0.191 mmol, 95.7%).

Source