Synthesis of 5-amino-α-D-gluco-hept-6-enfuranose as usefull 1-deoxynojirimycin precursor using [3,3]-sigmatropic aza-Claisen rearrangement

J. Gonda; M. Martinková; J. Elečko

doi:10.3390/ecsoc-14-00418

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Synthesis of 5-amino-α-D-gluco-hept-6-enfuranose as usefull 1-deoxynojirimycin precursor using [3,3]-sigmatropic aza-Claisen rearrangement

J. Gonda

M. Martinková

J. Elečko

¹ Department of Organic Chemistry, Institute of Chemistry, Faculty of Science, P.J. Šafárik University, Moyzesova 11., 040 01, Košice, Slovak Republic

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-14-00418

Abstract: Iminosugars are one of the most interesting discoveries in the field of natural products recent years due to their promissing biological activity. We report synthesis of 1-deoxynojirimycin building block using D-glucose as the starting material and the [3,3]-sigmatropic aza-Claisen rearrangement as the key step of our synthesis.

Keywords: 1-deoxynojirimycin, azasugars, aza-Claisen rearrangement

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J. Gonda

M. Martinková

J. Elečko