Synthesis and evaluation of glycosidase inhibitory activity of N-butyl 1-deoxy-d-gluco-homonojirimycin and N-butyl 1-deoxy-l-ido-homonojirimycin

Conjugate addition of n-butyl amine to d-glucose derived α,β-unsaturated ester 4 afforded β-amino esters 5a,b that on reduction of ester group, 1,2-acetonide deprotection, and reductive amination led to the formation of corresponding N-butyl 1-deoxy-d-gluco-homonojirimycin 2c and N-butyl 1-deoxy-l-ido-homonojirimycin 2d which were found to be selective β-glucosidase inhibitors with an IC50 value in millimolar range.

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