ABSTRACT
Iminosugars form a class of carbohydrate mimics of increasing importance.1 Historically known as potent glycosidase inhibitors,2 the scope of their biological activity has been extended recently to a diversity of enzymes such as glycosyltransferases,3 glycogen phosphorylases,4 and nucleoside-processing enzymes.5 As a consequence, iminosugars are now lead compounds for the treatment of a variety of diseases including diabetes,6 cancers,7 viral infections,8 and rare genetic diseases (lysosomal storage disorders9 and cystic ¥brosis10). The recent approval of ZavescaTM as the ¥rst oral treatment for Gaucher disease, a rare glycosphingolipidose, is a remarkable demonstration of the importance of iminosugars as medicines
Introduction ............................................................................................................ 259 Experimental Methods ........................................................................................... 261
General Methods ............................................................................................... 261 1,5-Di-(1/2-Benzotriazolyl)-N-Benzyl-1,5-Dideoxy-1,5-Iminoxylitol (4) ... 261 2,3,4-Tri-O-Acetyl-1,5-Di-C-Allyl-N-Benzyl-1,5-Dideoxy-1,5Iminoxylitol (5) ............................................................................................ 262 Meso-(1R,5S)-, Meso-(1S,5R)-, and Rac-(1R,5R)-2,3,4-Tri-O-Acetyl1,5-Di-C-Allyl-1,5-Dideoxy-1,5-Iminoxylitol (6a, 6b, and 6c)................... 262
Acknowledgment ................................................................................................... 263 References .............................................................................................................. 267
for unmet medical needs.9 In this context, the development of rapid and general access to original iminosugars is highly needed.
