An efficient method for the stereoselective synthesis of N-substituted trihydroxypiperidine derivatives promoted by p-TsOH

TETRAHEDRON

卷:72

Article

Yuan, Wen^1,3  Xia, Jianhui²  Zhang, Xiaoke^1,3  Liang, Peng^1,3  Zhang, Jichao^1,3  Jiao, Wei¹  Shao, Huawu¹ 

[1] Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu, Peoples R China

[2] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang, Jiangxi, Peoples R China

[3] Univ Chinese Acad Sci, Beijing, Peoples R China

关键词: Trihydroxypiperidine;    Mannich-type reaction;    p-TsOH;    Iminosugars;    Glucosidase inhibitors;   

DOI  :  10.1016/j.tet.2016.05.023

来源: Elsevier

【 摘 要 】

An effective and facile method for the synthesis of N-substituted trihydroxypiperidine derivatives is described. The Mannich-type reaction of protected 5-O-tosylate pentoses with amines and ketones in the presence of p-TsOH provides convenient access to the stereoselective synthesis of N-substituted iminosugar C-glycosides as potential glucosidase inhibitors in good to excellent yields. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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