Triethylamine → 6-N-(4-Monomethoxytrityl)-9-(2-deoxy-5-O-(4-monomethoxytrityl)-beta-L-erythropentofuranosyl)adenine

Participants

Reaction Conditions

Reaction Steps

A solution of the crude mixture 8, palladium acetate (3.44 g), triphenylphosphine (8.0 g) in N-methylpyrolidinone (1375 ml) with triethylamine (4.3 ml) was stirred at room temperature for 45 min. Then, tetramethyltin (42.4 ml) was added dropwise at 0C under argon. After stirring at 100-110° C. overnight, the reaction mixture was poured into water and extracted with diethyl ether. The organic solution was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography [eluant: stepwise gradient of ethyl acetate (0-10%) in toluene] to give compound 9 as a foam (42.3 g, 48.3% for the 2 steps). 1H NMR (DMSO) δ ppm 0.8.3-7.2 (m, 15H,2 C6H5CO, 1 CH3C6H4CO, H-6), 6.29 (t, 1H, H-1′, J=7.0 Hz), 5.7 (m, 1H, H-3′), 4.7-4.5 (m, 3H, H-5′, H5″, H-4′), 2.7-2.6 (m, 2H, H-2′, H-2″); FAB<0, (GT) m/e 567 (M−H)−, 449 (M−CH3C6H4CO)−, 243 (B)−, 121 (C6H5COO)−; FAB>0 (GT) 1137 (2M+H)+, 569 (M+H)+, 325 (M−B)−, 245 (B+2H)+, 119 (CH3C6H5CO)−;

Provenance & Evidence