791067-02-2Relevant academic research and scientific papers
Synthesis and chemistry of noeuromycin and isofagomine analogues
Liu, Huizhen,Lillelund, Vinni H.,Andersch, Jens,Liang, Xifu,Bols, Mikael
, p. 223 - 238 (2007/10/03)
Several N-substituted analogues of noeuromycin ((2RS,3S,4R,5R)-2,3,4- trihydroxy-5-hydroxymethylpiperidine) and isofagomine ((3R,4R,5R)-3,4-dihydroxy- 5-hydroxy-methylpiperidine) were synthesised. The isofagomine analogues (3RS,4RS,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxymethyl-piperidine, (3SR,4SR,5RS)-N-(2-phosphonoethyl)-3,4-dihydroxy-5-hydroxy-methylpiperidine, and (3R,4R,5R)-N-(10-chloro-9-anthracenemethyl)-3,4-dihydroxy-5-hydroxy- methylpiperidine were synthesised by direct alkylation of the corresponding azasugar. N-Substituted noeuromycin derivatives could not be made in this straightforward manner, but were made by modification of a synthesis intermediate. By this method (2RS,3S,4R,5R)-N-(4-methoxyphenyl)-2,3,4- trihydroxy-5-hydroxymethylpiperidine and (2RS,3S,4R,5R)-N-nonyl-2,3,4- trihydroxy-5-hydroxymethylpiperidine were synthesised. The stability of noeuromycin was studied and was found to depend on stereochemistry and pH. The L-fuco isomer ((2RS,3R,4R,5R)-2,3,4-trihydroxy-5-methylpiperidine) was observed to undergo a particularly facile Amadori rearrangement at neutral pH to the 3-ketopiperidine. A noeuromycin analogue, that could not undergo the Amadori rearrangement, was synthesised. Copyright
