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Synthesis of 1,4-dideoxy-1,4-iminoheptitol and 1,5-dideoxy-1,5-iminooctitols from D-xylose. 2010

Amit Kumar, and Mohammed Abrar Alam, and Shikha Rani, and Yashwant D Vankar
Department of Chemistry, Indian Institute of Technology, Kanpur, India.

The synthesis of iminosugars from inexpensive D-xylose in high yields has been developed. The key step in this synthesis involves Wittig olefination or chelation-controlled attack of Grignard reagents on lactol and ring-closing metathesis using first or second generation Grubbs' catalysts.

UI MeSH Term Description Entries
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D005690 Galactose An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Deficiency of galactosyl-1-phosphate uridyltransferase (GALACTOSE-1-PHOSPHATE URIDYL-TRANSFERASE DEFICIENCY DISEASE) causes an error in galactose metabolism called GALACTOSEMIA, resulting in elevations of galactose in the blood. D-Galactose,Galactopyranose,Galactopyranoside,D Galactose
D006026 Glycoside Hydrolases Any member of the class of enzymes that catalyze the cleavage of the glycosidic linkage of glycosides and the addition of water to the resulting molecules. Endoglycosidase,Exoglycosidase,Glycohydrolase,Glycosidase,Glycosidases,Glycoside Hydrolase,Endoglycosidases,Exoglycosidases,Glycohydrolases,Hydrolase, Glycoside,Hydrolases, Glycoside
D014994 Xylose D-Xylose,D Xylose
D050111 Imino Sugars Sugars in which the OXYGEN is replaced by a NITROGEN atom. This substitution prevents normal METABOLISM resulting in inhibition of GLYCOSIDASES and GLYCOSYLTRANSFERASES. Sugars, Imino

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