76670-93-4Relevant academic research and scientific papers
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.
A Convenient, Gram-Scale Synthesis of 1-Deoxymannojirimycin
Stauffert, Fabien,Lepage, Mathieu L.,Pichon, Ma?va M.,Hazelard, Damien,Bodlenner, Anne,Compain, Philippe
supporting information, p. 1177 - 1180 (2016/05/11)
A novel gram-scale synthesis of 1-deoxymannojirimycin from tetra-O-benzyl-d-glucopyranose in 9 steps and 28% overall yield with a limited number of purification steps is reported. The synthetic strategy is based on the regioselective deprotection and subs
Synthesis of glycosylamines and glyconamides using molecular iodine
Fusaro, Maxime B.,Chagnault, Vincent,Postel, Denis
, p. 542 - 550 (2013/07/27)
We describe herein the synthesis of glyconamides and glycosylamines usingmolecular iodine on benzylated carbohydrates. During the improvement and the optimization of the direct oxidative amidation reaction,we also discovered the possibility to form glycosylamines with excellent yields and short reaction times in comparison with the previously reported procedures. Advantages of these methods are the operational simplicity, elimination of use of complicated reagents and procedures, and generality of the reactions. Our methodology is an excellent access to precursors of N-alkyliminosugars and imino-C-glycosides.
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
experimental part, 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.
Efficient synthesis of 1-deoxy-azasugars as useful synthetic tools
Sawada, Daisuke,Takahashi, Hideyo,Ikegami, Shiro
, p. 3085 - 3088 (2007/10/03)
1-Deoxy-azasugars are efficiently prepared from sugar-lactones using a stereoinversion process and they are applied to the synthesis of a natural product.
Direct oxidative amidation of aldoses by iodine in ammonia water
Chen, Ming-Yi,Hsu, Jue-Liang,Shie, Jiun-Jie,Fang, Jim-Min
, p. 129 - 133 (2007/10/03)
Aldopentoses, aldohexoses and the benzylated derivatives reacted with iodine in ammonia water at room temperature to give their corresponding saccharide amides in high yields. The reactions proceeded with oxidation of the aldose hemiacetals by iodine to g
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.
