Synthesis and glycosidase inhibitory activity of new penta-substituted C8-glycomimetics

The syntheses of new C8-carbasugars and -aminocyclitols related to miglitol and voglibose are described. The key step involves the ring closing metathesis of 1,9-dienes derived from D-mannitol. Chemical transformations of the newly created double bond of the resulting cyclooctenes involved notably hydroboration and reductive amination. The inhibitory activity of the glycomimetics so-obtained has been evaluated towards 24 commercially available glycosidases. (c) 2005 Elsevier Ltd. All rights reserved.


Published in:
Tetrahedron, 61, 30, 7094-7104
Year:
2005
ISSN:
0040-4020
Keywords:
Note:
Univ Paris 05, CNRS, UMR 8601, Lab Chim & Biochim Pharmacol & Toxicol, F-75270 Paris, France. Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, BCH, CH-1015 Lausanne, Switzerland.
Other identifiers:
Laboratories:




 Record created 2005-11-09, last modified 2018-03-17


Rate this document:

Rate this document:
1
2
3
 
(Not yet reviewed)