Cytarabine → N4-[N-(cholest-5-en-3beta-oxycarbonyl)glycyl]-1-beta-D-arabinofuranosylcytosine

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(cholest-5-en-3β-oxycarbonyl)glycine (2.74 g) and triethylamine (0.78 ml) in tetrahydrofuran (40 ml) was added dropwise ethyl chlorocarbonate (0.61 g) at -15° C., and the reaction mixture was stirred for 20 minutes at -15° C. To the reaction mixture a solution of 1-β-D-arabinofuranosylcytosine (1.37 g) in dimethylformamide (30 ml) was added dropwise at -15° C. to -10° C. After the addition, the mixture was stirred for one hour at 5° C. and then for 30 minutes at room temperature. The reaction mixture was concentrated in vacuo. The residue was washed with methanol and dried to afford a crude reaction product, which was purified by silica gel column chromatography to yield N4 -[N-(cholest-5-en-3β-oxycarbonyl)glycyl]-1-β-D- arabinofuranosylcytosine (1.8 g) as a white powder.

Provenance & Evidence