文献类型：期刊文献

英文题名：Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) and N-octyl-4-epi-β-valienamine (NOEV) from (-)-shikimic acid

作者：Li, Feng-Lei[1];Yu, Jiang-Ping[1];Ding, Wei[1];Sun, Mian-Mian[1];He, Yun-Gang[1];Zhu, Xing-Liang[1];Liu, Shi-Ling[2];Shi, Xiao-Xin[1]

机构：[1]East China Univ Sci & Technol, Minist Educ, Engn Res Ctr Pharmaceut Proc Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China;[2]Shanghai Qingping Pharmaceut Co Ltd, 397 Zhao Jiang Rd, Shanghai 201710, Peoples R China

年份：2019

卷号：9

期号：72

起止页码：42077

外文期刊名：RSC ADVANCES

收录：;EI(收录号：20200107980949);WOS:【SCI-EXPANDED(收录号:WOS:000516545700012)】；

基金：We are grateful to the National Natural Science Foundation of China (No. 20972048) for the financial support of this work.

语种：英文

外文关键词：Carboxylic acids

摘要：N-Octyl-beta-valienamine (NOV) 1 and N-octyl-4-epi-beta-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 via 9 steps in 50% yield. Compound 5 was then converted to NOV 1via 5 steps in 61% yield, and it was also converted to NOEV 2via 8 steps in 38% yield. In summary, NOV 1 was synthesized via 14 steps in 31% overall yield; and NOEV 2 was synthesized via 17 steps in 19% overall yield.