- 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 foun...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1016/j.tetasy.2012.03.007
-
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- Journal:
- TETRAHEDRON-ASYMMETRY
- Volume:
- 23
- Issue:
- 5
- Pages:
- 401-408
- Publication date:
- 2012-03-15
- DOI:
- EISSN:
-
1362-511X
- ISSN:
-
0957-4166
- URN:
-
uuid:0deca802-725b-4e0e-ad13-7b5ff8e7bccc
- Source identifiers:
-
329995
- Local pid:
- pubs:329995
- Language:
- English
- Copyright date:
- 2012
Journal article
Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3.4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2
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