A Short and Simple Synthesis of 1-Deoxynojirimycin Derivatives from d-Glucose

Roy Ashim. Achari Basudeb. Mandal SukhenduB.. Synthesis  2006,  1035 

The synthesis of deoxynojirimycin derivatives from d -glucose requires a double inversion at C-5. In the paper cited above, we described a single inversion at C-5 and consequently, compounds 9, 10 and 11 must be epimers at C-5 of the structures shown. Therefore, the title, abstract and structures of 9, 10, and 11 should be amended as follows:

Title: A Synthesis of 1-Deoxy-l-ido-nojirimycin Derivatives from d-Glucose

Abstract: Insertion of an amino functionality at C-5 of d-glucose with inversion of configuration, followed by imine formation with the latent aldehyde at C-1 and concomitant reduction, furnished the 1-deoxy-l-ido-nojirimycin skeleton.Correct structures of compounds 9, 10 and 11 are shown below:

We would also like to point out that a closely related synthesis of 1-deoxynojirimycin from 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-l-ido-furanose has been described: Fleet, G. W. J.; Carpenter, N. M.; Petursson, S.; Ramsden, N. G. Tetrahedron Lett. 1990, 31, 409 (cited as reference 8b).