摘要
报道了一条合成(3S,4S)-4-氨基-3-羟基-5-苯基戊酸(Ahppa)衍生物的新路线。以氨基保护的L-苯丙氨酸为起始原料,依次经Weinreb胺缩合、还原、aldol缩合及溴仿4步反应合成了3个Ahppa衍生物,总收率5.8%-6.7%,其结构经^1H NMR,^13C NMR和ESI-MS确证。对反应条件进行了探讨,结果表明:催化剂D-脯氨酸用量对反应收率影响不大,对立体选择性影响较大;氨基上保护基体积较大有利于提高反应立体选择性。
A new route for the synthesis of (3S ,4S)-4-amino-3-hydroxy-5-phenylpentanoic acid derivatives was reported. The target compounds with overall yields of 5.8% - 6.7% were synthesized by condensation with Weinreb amide, reduction, aldol condensation reaction and bromine imitation reaction, using amino-protected L-phenylalanine as starting material. The structures were confirmed by ^1H NMR, ^13C NMR and ESI-MS. The exploration of reaction conditions showed that the loading amount of D-proline had no evident effect on the yield, but on stereoselectivity. Larger size protecting groups in substrate can enhanced the stereo-selectivity.
出处
《合成化学》
CAS
CSCD
2016年第4期355-358,共4页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(81573340)
复旦大学卓学人才计划资助项目