以（-）-莽草酸为原料立体选择性合成新辛基-β-缬氨烯胺（NOV）和新辛基-4-脱氧-β-缬氨烯胺（NOEV） 。
Novel stereoselective syntheses of -octyl-β-valienamine (NOV) and -octyl-4--β-valienamine (NOEV) from (-)-shikimic acid.
作者信息
Li Feng-Lei, Yu Jiang-Ping, Ding Wei, Sun Mian-Mian, He Yun-Gang, Zhu Xing-Liang, Liu Shi-Ling, Shi Xiao-Xin
机构信息
Engineering Research Center of Pharmaceutical Process Chemistry of the Ministry of Education, East China University of Science and Technology 130 Mei-Long Road Shanghai 200237 P. R. China
Shanghai Qingping Pharmaceutical Co. Ltd. 397 Zhao-Jiang Road, Baihe Town, Qingpu District Shanghai 201710 P. R. China
出版信息
RSC Adv. 2019 Dec 18;9(72):42077-42084. doi: 10.1039/c9ra09235h.
-Octyl-β-valienamine (NOV) 1 and -octyl-4--β-valienamine (NOEV) 2 are potent chemical chaperone drug candidates for the therapy of lysosomal storage disorders. Novel stereoselective syntheses of NOV 1 and NOEV 2 starting from naturally abundant (-)-shikimic acid are described in this article. The common key intermediate compound 5 was first synthesized from readily available (-)-shikimic acid 9 steps in 50% yield. Compound 5 was then converted to NOV 1 5 steps in 61% yield, and it was also converted to NOEV 2 8 steps in 38% yield. In summary, NOV 1 was synthesized 14 steps in 31% overall yield; and NOEV 2 was synthesized 17 steps in 19% overall yield.
-辛基-β-缬氨酰胺（NOV）1和-辛基-4--β-缬氨酰胺（NOEV）2是用于治疗溶酶体贮积症的强效化学伴侣药物候选物。本文描述了从天然丰富的（-）-莽草酸开始对NOV 1和NOEV 2进行的新型立体选择性合成。常见的关键中间体化合物5首先由易得的（-）-莽草酸经9步反应以50%的产率合成。然后化合物5经5步反应以61%的产率转化为NOV 1，也经8步反应以38%的产率转化为NOEV 2。总之，NOV 1经14步反应以31%的总产率合成；NOEV 2经17步反应以19%的总产率合成。
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