Carbohydrate Research 1996-06-07

A novel approach to the 1-deoxynojirimycin system: synthesis from sucrose of 2-acetamido-1, 2-dideoxynojirimycin, as well as some 2-N-modified derivatives.

G Gradnig, G Legler, A E Stütz

Index: Carbohydr. Res. 287(1) , 49-57, (1996)

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Abstract

6-Azido-1,3,4-tri-O-benzyl-6-deoxy-D-fructofuranose can be easily obtained in two steps from the known 6,6'-diazido-6,6'-dideoxysucrose (available in two steps from sucrose) and cyclized by controlled hydrogenation and concomitant intramolecular reductive amination to give 3,4,6-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol, a partially protected derivative of 1-deoxymannojirimycin. After N-protection, position 2 is regio-specifically available to modification. This novel approach was taken advantage of in a synthesis of 2-acetamido-1,2- dideoxynojirimycin and new analogues thereof. Results of inhibition studies conducted with these new compounds employing N-acetylhexosaminidases of various sources are discussed.