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一种高效合成醛己糖衍生的哌啶硝酮的方法：哌啶亚氨基糖的前体。

An efficient synthesis of aldohexose-derived piperidine nitrones: precursors of piperidine iminosugars.

机构信息

Beijing National Laboratory for Molecular Science, CAS Key Laboratory of Molecular Recoganition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

出版信息

Molecules. 2013 May 21;18(5):6021-34. doi: 10.3390/molecules18056021.

DOI:10.3390/molecules18056021
PMID:23698053
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6270483/
Abstract

D-glucopyranose-derived and L-idopyranose-derived piperidine nitrones were synthesized in good overall yields through six-step reaction sequence starting from readily available 2,3,4,6-tetra-O-benzyl-D-glucopyranose. The method is efficient and could be general for the synthesis of aldohexose-derived piperidine nitrones which are precursors of piperidine iminosugars.

摘要

从 2,3,4,6-四-O-苄基-D-吡喃葡萄糖出发，经六步反应得到了 D-吡喃葡萄糖衍生和 L-吡喃糖衍生的哌啶亚硝酮，总收率良好。该方法效率高，可广泛应用于醛己糖衍生的哌啶亚硝酮的合成，后者是哌啶亚氨基糖的前体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/5feee1bc61ae/molecules-18-06021-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/895cf6f6358e/molecules-18-06021-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/ce396d82c836/molecules-18-06021-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/56ec2d33a0a7/molecules-18-06021-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/5feee1bc61ae/molecules-18-06021-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/895cf6f6358e/molecules-18-06021-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/ce396d82c836/molecules-18-06021-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/56ec2d33a0a7/molecules-18-06021-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/86a7/6270483/5feee1bc61ae/molecules-18-06021-g004.jpg

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本文引用的文献

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Synthesis of a chiral C2-symmetric sterically hindered pyrrolidine nitroxide radical via combined iterative nucleophilic additions and intramolecular 1,3-dipolar cycloadditions to cyclic nitrones.通过联合迭代亲核加成和分子内环加成反应合成手性 C2 对称位阻吡咯烷氮氧自由基到环状硝酮。
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