Miglustat was originally discovered at Searle (now
Pfizer) and an enzymatic oxidation was employed in the
synthesis. D-Glucose (125) was subjected to reductive
amination with n-butylamine in ethanol under 4 atm of
hydrogen in the presence of Pd/C catalyst at 60 oC to give
N-butylglucamine HCl salt (126) in 90% yield. Nbutylglucamine
(126) then was submitted to a selective
microorganism oxidation by Gluconobacter Oxidans (DSM
2003) cell paste in water to give 6-(butylamino)-6-deoxy-a-
L-sorbofuranose HCl salt (127) in 80 % yield. Finally,
compound 127 was cyclized and reduced in situ with
hydrogen over Pd/C at 4000 atm in ethanol/water to give
miglustat (XVI) in 45% overall yield from D-glucose (125).
