Medicinal Chemistry

An Improved Synthetic Method for N-Butyl-1-Deoxynojirimycin

Abstract

Jiajia Wang, Yunyan Zhao, Wei Zhao, Peng Wang and Jing Li

N-butyl-1-deoxynojirimycin (NB-DNJ) based on imino sugars Deoxynojirimycin (DNJ) has been approved for treatment of Gaucher’s disease. Here, an improved synthetic procedureof NB-DNJ was described. High yields can be achieved during the introduction steps of n-butyl by combining a strong nucleophilicity of imine in the iminosugar andan easy leaving group methanesulfonatein butyl, which is much higher than the similar reported procedures. This method can be served as an excellent solution to the synthesis of various N-alkyl substituted chain DNJ, even applied to large-scale production.