862822-65-9Relevant academic research and scientific papers
Synthesis and glycosidase inhibitory activity of new penta-substituted C8-glycomimetics
Andriuzzi, Olivia,Gravier-Pelletier, Christine,Vogel, Pierre,Le Merrer, Yves
, p. 7094 - 7104 (2005)
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.
Efficient route to optically pure polyfunctionalized cyclooctanes
Gravier-Pelletier, Christine,Andriuzzi, Olivia,Le Merrer, Yves
, p. 245 - 248 (2007/10/03)
A short and efficient synthesis of enantiopure highly functionalized eight-membered carbocyclic rings is described from 1,2:5,6-bis-epoxides issued from d-mannitol. The key cyclization step involves the metathesis of 1,9-diene using Grubbs' catalyst or the pinacolic coupling of 1,8-dialdehyde resulting from the oxidative cleavage of the previous diene. In the specific case of ring-closing metathesis cyclization, the influence of a conformationally restricted diene compared to that of a flexible one has been evaluated.
