反応 #582496

ord-13c764d90a0b40dfad62e937ef405219

反応方程式

CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO
D-erythro-sphingosine
CC(=O)OC(C)=O
acetic anhydride
→
CC(=O)C(CCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO)(C(C)=O)C(C)=O
133
CC(=O)C(CCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO)(C(C)=O)C(C)=O
Triacetylsphingosine

反応物

CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO
D-erythro-sphingosine
CC(=O)OC(C)=O
acetic anhydride

試薬

なし

溶媒

c1ccncc1
pyridine

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The solvent was removed by a stream of nitrogen

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: USRE038793E1uspto-grants-2005_09