Chlorosuccinimide → (Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

Participants

Reaction Conditions

Reaction Steps

Dibenzyl chlorophosphate was prepared by adding N-chlorosuccinimide (2.2 g) to a solution of dibenzylphosphite (4.4 g) in dry toluene (70 ml) at room temperature with stirring. The resulting solid was filtered off and the filtrate concentrated to ca. 10 ml. and added to a solution of 4′-methoxyphenyl 2,3,4-tri-O-acetylmannoside (3.86 g) in pyridine (30 ml) at 0° C. and the mixture allowed to stand over night. The mixture was warmed to 40° C. for 1 h and the solvent evaporated under reduced pressure. The residue was chromatographed on a silica gel 60 chromatography column (2.5×55 cm). The column was first eluted with CHCl3 and this fraction discarded. Subsequent elution with 20% acetone/CHCl3 gave 4′-methoxyphenyl 2,3,4-tri-O-acetylmannoside dibenzylphosphate (2.9 g). (1Hnmr, CDCl3: 2.06, s, 3H; 2.09, s, 3H; 2.13, s, 3H; 3.53, t, 1H; 3.6, s, 3H; 3.88, t, 1H; 3.97, m, 1H; 4.8, d, 1H; 5.12, m, 1H; 5.3, m, 2H; 6.81, d, 2H; 6.97, d, 2H; 7.3, m, 10H.) Starting material (1.46 g) was recovered from the column by elution with 10% EtOH/CHCl3.

Provenance & Evidence