| 摘要 |
PURPOSE:To provide a production method for asymmetrically synthesizing natural type sphingosine and analog compound thereof preferentially, more simply through fewer reaction steps and in a high diastereoisomerism selectivity. CONSTITUTION:A compound of the formula I (R1 and R2 are each H, an aryl or a lower alkyl; X is a urethane type, an acyl type or an alkyl type N- protecting residue) such as 1,1-dimethylethyl (S)-4-formy1-2,2-dimethyl-3- oxazolidinecarboxylate is reacted with a zinc compound of the formula II (R3 is a lower alkyl; R4 is a 4-21C alkenyl) such as 1-pentadecenylmethyl (or ethyl) zinc in the presence of a catalyst and then hydrolyzed to give a compound of the formula III. A chiral catalyst of (R) or (S)-diphenyl (1-methyl-2- pyrrolidinyl) methanol or an achiral catalyst selected from an amino-alcohol- based catalyst, a diamine-based catalyst and a Lewis acid is used as the catalyst used in the reaction. The amine functional group of the compound of the formula III is acylated to give a natural type ceramide. |
