Acetic Anhydride → 3-acetyl-3-[(E,15R,16S)-16-amino-15,17-dihydroxyheptadec-13-enyl]pentane-2,4-dione

Participants

Reaction Steps

In a procedure similar to Grode and Cardellina,93 D-erythro-sphingosine (4, 2 mg, 6.7 μmol, Sigma) in acetic anhydride (1 mL) and pyridine (2 mL) was stirred at 25° C. for 4.5 h, at which time no starting material could be observed by TLC. The solvent was removed by a stream of nitrogen to give 133: white solid; silica TLC Rf 0.86 (3:12:2:2 CHCl3/1-BuOH/AcOH/H2O, phosphomolybdic acid), 0.65 (9:1 CHCI3/MeOH, phosphomolybidic acid); FABMS m/z 580, 426, 366, 306, 264; CIMS m/z 468, 454, 426, 424, 394, 366, 364, 306, 264, 144, 85, 84, 83, 61.

Provenance & Evidence