M. Simone, R. Soengas, S. F. Jenkinson
Mar 15, 2012
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Influential Citations
19
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Homochiral piperidines containing a quaternary carbon branch at C-2 of the piperidine ring may be made from readily available carbohydrate lactones containing a branched 2-C-hydroxymethyl substituent. This gives an easy access to the branched iminosugars. In particular a trihydroxypipecolic acid analogue, (3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid, has been synthesised efficiently from the starting material d -ribose and (3S,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol was found to be a specific inhibitor of α- d -glucosidase from Bacillus Stearothermophilus with an IC50 value of 93 μM.