1,2-Dichloroethane → 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide

Participants

Reaction Steps

A stirred solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (50.3 g, 80 mmol), 1,2-dichloroethane (100 ml), and cyanotrimethylsilane (15.84 g, 160 mmol) was treated in one portion via a syringe with anhydrous stannic chloride (20.8 g, 9.33 ml, 80 mmol). The darkening solution was stirred for two minutes then poured into saturated sodium hydrogen carbonate (800 ml), and stirred five minutes (pH 7). Chloroform (1 liter) was added and the emulsion was filtered through Celite®. The chloroform layer was separated, dried (MgSO4) and evaporated under reduced pressure (15 torr, 40° ) to a light orange syrup which was crystallized from ethanol (charcoal to afford 2 (30 g from two crops, 80%) as long white needles; mp 77°-78° after drying at 0.05 torr, 60° for two hours; [α]D25 +24.4° (0.5 CHCl3).

Provenance & Evidence