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

Simone, M; Soengas, R; Jenkinson, S; Evinson, E; Nash, R; Fleet, G

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

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 IC 50 value of 93 μM. © 2012 Elsevier Ltd. All rights reserved.

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APA Style

Simone, M., Soengas, R., Jenkinson, S., Evinson, E., Nash, R., & Fleet, G. (2012). 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. TETRAHEDRON-ASYMMETRY, 23(5), 401–408.

MLA Style

Simone, M., et al. “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.” TETRAHEDRON-ASYMMETRY, vol. 23, no. 5, 2012, pp. 401–08.

Chicago Style

Simone, M, R Soengas, S Jenkinson, E Evinson, R Nash, and G Fleet. 2012. “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.” TETRAHEDRON-ASYMMETRY 23 (5): 401–8.
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