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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

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...

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Publication status:
Published

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Authors


Simone, MI More by this author
Soengas, RG More by this author
Jenkinson, SF More by this author
Evinson, EL More by this author
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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

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