Azobisisobutyronitrile → N6-Benzoyl-5'-O-tert-butyldimethylsilyl-2',3'-dideoxy-3'-ethylacrylyladenosine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

N6 -Benzoyl-5'-O-tert-butyldimethylsilyl-2,'3'-dideoxy-3'-ethylacrylyladenosine (Compound 10, Table III) was prepared by dissolving N6 -Benzoyl-5'-O-tert-butyldimethylsilyl-2'-deoxy-3'-O-phenoxythiocarbonyladenosine (50 mg, 0.08 mmole), cis-ethyl-3-tributylstannyl-2-propenoate (92 mg, 0.236 mmole) and hexamethylditin (13 mg, 0.04 mmole) in 2 ml toluene in a 40 ml Schlenk tube, and then adding 15 mg (0.11 mmole) azo-bis-isobutyronitrile to the mixture. The resulting mixture was freeze-pump-thaw degassed 3 times and then heated at 87° C. in an oil bath for 3 days. Approximately every 12 hours, fresh 15 mg azo-bisisobutyronitrile was added to the reaction. Following the 3-day incubation period, the reaction was cooled, the solvent evaporated, and the residue chromatographed with 1% ethanol in dichloromethane as eluent. A yield of 19 mg N6 -Benzoyl-5'-O-tert-butyldimethylsilyl-2',3'-dideoxy-3'-ethylacrylyladenosine was obtained as a white solid after evaporation of the appropriate fractions (42% yield).

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