Synthesis of 1,2-cis-Homoiminosugars Derived from GIcNAc and GaINAc Exploiting a β-Amino Alcohol Skeletal Rearrangement

被引：30

作者：

Bleriot, Yves ^{[1
]}

Auberger, Nicolas ^{[1
]}

Jagadeesh, Yerri ^{[1
]}

Gauthier, Charles ^{[1
]}

Prencipe, Giuseppe ^{[2
]}

Anh Tuan Tran ^{[2
]}

Marrot, Jerome ^{[3
]}

Desire, Jerome ^{[1
]}

Yamamoto, Arisa ^{[4
]}

Kato, Atsushi ^{[4
]}

Sollogoub, Matthieu ^{[2
]}

机构：

[1] Univ Poitiers, Glycochem Grp, Organ Synth Team, UMR 7285,IC2MP,CNRS, F-86073 Poitiers 9, France

[2] Univ Paris 06, Sorbonne Univ, Inst Univ France, UMR 8232,IPCM,LabEx MiChem,CNRS, F-75005 Paris, France

[3] Univ Versailles, UMR 8180, CNRS, Inst Lavoisier Versailles, F-78035 Versailles, France

[4] Toyama Univ, Dept Hosp Pharm, Toyama 9300194, Japan

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 21期

关键词：

IMINOSUGAR C-GLYCOSIDES; MIMICKING MONOSACCHARIDES; ALPHA-HOMONOJIRIMYCIN; D-GLUCOSE; POTENT; INHIBITORS; 2-ACETAMIDO-1,2-DIDEOXYNOJIRIMYCIN; ACCESS; 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL; ISOMERIZATION;

D O I：

10.1021/ol502926f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：5512 / 5515

页数：4

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