Acetyl chloride → 9-(5-O-acetyl-beta-D-arabinofuranosyl)adenine

Participants

Reaction Steps

To a stirred mixture of 2.67 g. of 9-(β-D-arabinofuranosyl)adenine and 100 ml. of 1:1 dimethylformamide-pyridine is added 0.79 g. of acetyl chloride at 25° C. The mixture is stirred, while being protected from moisture, for 1.5 hours, then treated with 50 g. of crushed ice and evaporated at reduced pressure. The residue is added to a 3× 40 cm. column of dry silica gel and the column is eluted sequentially with 500-ml. portions of 5, 10, 15 and 20% (v/v) methanol in chloroform. Two fractions of eluate (the 15 and 20% methanol in chloroform eluates) are combined and evaporated at reduced pressure to give the desired product 9-(5-O-acetyl-β-D-arabinofuranosyl)adenine; m.p. 197.5°-198.5° C. after crystallization from ethanol, [α]D23 = +23.6° (c = 1% in methanol), λmaxCH3OH = 258 nm (ε = 15,000), water solubility: 9.9 mg./ml.

Provenance & Evidence