76670-94-5Relevant articles and documents
Synthesis of 1-deoxynojirimycin: Exploration of optimised conditions for reductive amidation and separation of epimers
Iftikhar, Mehwish,Wang, Lin,Fang, Zhijie
, p. 460 - 464 (2017/08/18)
1-Deoxynojirimycin (DNJ), which has importance with respect to sugar processing enzymes, is a synthetic target for chemists. A key step in the synthesis of DNJ is the preparation of 2,3,4,6-tetra-O-benzyl-D-glucono-δ-lactam. By varying reaction parameters such as temperature, solvent and reducing reagent, improvements on previous methods are described. A novel approach for the synthesis of 2,3,4,6-tetra-O-benzyl-5-dehydro-5-deoxo-D-gluconamide has been developed by using PCC as an oxidising agent. Separation of epimers permitted DNJ to be obtained in 85% yield after reduction and hydrogenolysis steps.
Total synthesis of N-butyl-1-deoxynojirimycin
Wang, Jiajia,Zhao, Yunyan,Zhao, Wei,Wang, Peng,Li, Jing
, p. 445 - 454 (2017/08/23)
N-Butyl-1-deoxynojirimycin (NB-DNJ) derived from imino sugar deoxynojirimycin (DNJ) has been approved for the treatment of Gaucher’s disease. Herein, a facile and efficient synthetic procedure for NB-DNJ has been described. Comparing to the methods reported previously,methanesulfonyl group was used as a leaving group for easy displacement upon attack by the imine in the sugar ring, leading to a high yield during the introduction of the n-butyl group. Thismethod can serve as an excellent protocol for the synthesis of DNJ derivatives with a variety of N-alkyl substituents and for large-scale production.
Structure-activity relationships in a series of C2-substituted gluco-configured tetrahydroimidazopyridines as β-glucosidase inhibitors
Li, Tiehai,Guo, Lina,Zhang, Yan,Wang, Jiajia,Zhang, Zhenxing,Li, Jing,Zhang, Wenpeng,Lin, Jianping,Zhao, Wei,Wang, Peng George
, p. 2136 - 2144 (2011/05/06)
Inhibition of glycoside hydrolases has widespread application in treatment of diabetes, viral infections, lysosomal storage diseases and cancers. Gluco-configured tetrahydroimidazopyridines are the most potent β-glucosidase inhibitors reported to date. Using transition state mimic strategy, a series of C2-substituted gluco-configured tetrahydroimidazopyridines were designed and synthesized. Compounds 3 (Ki = 0.64 nM) and 5 (Ki = 0.58 nM) showed stronger inhibitory potency against β-glucosidase. Maestro 9.1 was used to study the structure-activity relationships by docking the compounds into the β-glucosidase active sites. Crown Copyright
Glycosidase inhibition with fullerene iminosugar balls: A dramatic multivalent effect
Compain, Philippe,Decroocq, Camille,Iehl, Julien,Holler, Michel,Hazelard, Damien,Barragan, Teresa Mena,Mellet, Carmen Ortiz,Nierengarten, Jean-Francois
supporting information; experimental part, p. 5753 - 5756 (2010/10/21)
(Figure Presented) Superball ! A dodecavalent iminosugar derivative with a fullerene core (see picture) shows a binding enhancement of up to three orders of magnitude over the corresponding monovalent ligand in glycosidase inhibition assays. This is the first evidence of a significant multivalent effect in glycosidase inhibition.
A Facile Transformation of Sugar Lactones to Azasugars
Overkleeft, Herman S.,Wiltenburg, Jim van,Pandit, Upendra K.
, p. 4215 - 4224 (2007/10/02)
The synthesis of pyrano- and furano- sugar lactams from the corresponding lactones, in a five step sequence, is described.
An expedient stereoselective synthesis of gluconolactam
Overkleeft, Herman S.,Van Wiltenburg, Jim,Upendra Pandit
, p. 2527 - 2528 (2007/10/02)
An efficient synthesis of the title compound, starting from glucose, is described.
