ABSTRACT
The preparations of 1-deoxynojirimycin and N-substituted derivatives have long been of interest to the organic chemist. A literature search reveals that these compounds can be made by appropriately protecting the amino group of aminosorbitols, followed by selective microbial oxidation to give isolable 6-aminosorboses. The protecting groups can subsequently be removed either by catalytic hydrogenation or acidification followed by reductive intramolecular ring closure to form 1-deoxynojirimycin or its N-substituted derivatives. The available literature indicates that D-glucose and other sugars react with alkyl amines to give TV-alkylglucosides. It also reports that as a general class these compounds are labile and undergo rearrangement as well as hydrolysis. In addition to an improved synthesis of N-butylglucamine, we have outlined a three-step process for the conversion of D-glucose to N-butyl-l-deoxy-nojirimycin. The entire process is amenable to large-scale production with the following specific improvements.
