Triacetoxyperiodinane → HCID 10867910, compound

Participants

Reaction Steps

Compound (19) was prepared as described for compound (9). To a solution of 80 mmol of Cbz-O-Bn serinol (18) in 200 mL of dry dichloromethane, kept at room temperature under nitrogen, was added 88 mmol of Dess-Martin periodinane, and the reaction stirred for 2.5 hours, and then quenched by addition of 400 mL of 10% aqueous sodium thiosulfate solution. The layers were separated, and the organic layer concentrated, diluted with 300 mL of ethyl ether, and washed three times with a saturated aqueous bicarbonate solution containing 10% sodium thiosulfate, dried over magnesium sulfate, and concentrated. Compound (19) was obtained in 99% crude yield, and used without further purification. 1H NMR δ (CDCl3) 3.69-3.78 (dd, 1H, CH2O), 3.99-4.06 (dd, 1H, CH2O), 4.37-4.46 (m, 1H, CHN), 4.47-4.52 (d, 2H, CH2O), 5.14 (s, 2H, CH2O), 5.65-5.75 (br. d, 1H, NH), 7.14-7.48 (a series of m, 9H, Ph), 7.98-8.08 (dd, 1H, Ph), 9.63 (s, 1H, CHO).

Provenance & Evidence