Synthesis of 1,2-cis-Homoiminosugars Derived from GlcNAc and GalNAc Exploiting a 尾-Amino Alcohol Skeletal Rearrangement

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• 作者：Yves Bl茅riot ; Nicolas Auberger ; Yerri Jagadeesh ; Charles Gauthier ; Giuseppe Prencipe ; Anh Tuan Tran ; J茅r么me Marrot ; J茅r么me D茅sir茅 ; Arisa Yamamoto ; Atsushi Kato ; Matthieu Sollogoub
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：November 7, 2014
• 年：2014
• 卷：16
• 期：21
• 页码：5512-5515
• 全文大小：364K
• ISSN：1523-7052

文摘

The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these 伪-d-GlcNAc and 伪-d-GalNAc mimics utilizes a 尾-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring 伪-HGJ and 伪-HNJ. The 伪-d-GlcNAc-configured iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide. Preliminary glycosidase inhibition evaluation indicates that the 伪-d-GalNAc-configured homoiminosugar is a potent and selective 伪-N-acetylgalactosaminidase inhibitor.