Preparation of (5S)-5-C-methyl-β-L-lyxo-hexofuranose derivative as(+)-lactacystin precursors

J. Gonda; M. Martinková; D. Maliňák

doi:10.3390/ecsoc-14-00420

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Preparation of (5S)-5-C-methyl-β-L-lyxo-hexofuranose derivative as(+)-lactacystin precursors

J. Gonda

M. Martinková

D. Maliňák

¹ Department of Organic Chemistry, Institute of Chemical Science, Faculty of Science, P.J. Šafárik University in Košice, Moyzesova 11., 040 67, Košice, Slovakia

Published: 31 October 2010 by MDPI in The 14th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-14-00420

Abstract: We present here the preparation of the precursor for stereoselective synthesis of (+)-lactacystin starting from D-glucose. The first step is conversion of D-glucose to 1,2:5,6-di-O-isopropylidene-α-D-gulofuranose. The second step is introduction of a methyl group at C5 and preparation of compound 9. This compound can be used as a precursor of target molecule of (+)-lactacystin

Keywords: Lactacystin, Asymetric synthesis, Proteasome inhibitor

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J. Gonda

M. Martinková

D. Maliňák