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

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• 作者：Wen Yuan^a ; ^c ; Jianhui Xia^b ; Xiaoke Zhang^a ; ^c ; Peng Liang^a ; ^c ; Jichao Zhang^a ; ^c ; Wei Jiao^a ; Huawu Shao^a ; ^{shaohw@cib.ac.cn" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Trihydroxypiperidine ; Mannich-type reaction ; p-TsOH ; Iminosugars ; Glucosidase inhibitors
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：7 July 2016
• 年：2016
• 卷：72
• 期：27-28
• 页码：3994-4000
• 全文大小：725 K

文摘

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.