Synthesis of glycosylated 1-deoxynojirimycins starting from natural and synthetic disaccharides

Liu, B.; Mechelen, J. van; Berg, R.J.B.H.N. van den; Nieuwendijk, A.M.C.H. van den; Aerts, J.M.F.G.; Marel, G.A. van der; ... ; Overkleeft, H.S. (2018)

Article / Letter to editor

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bioorganic chemistry and medicinal chemistry, yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1‐deoxynojirimycin derivatives based on the oxidation–reductive amination protocol that in the past has also been shown to be a versatile route towards 1‐deoxynojirimycin. The strategy can be applied on commercial disaccharides, as shown in four examples, as well as on disaccharides that are not commercially available and are synthesized for this purpose, as shown by a fifth example.

• All authors: Liu, B.; Mechelen, J. van; Berg, R.J.B.H.N. van den; Nieuwendijk, A.M.C.H. van den; Aerts, J.M.F.G.; Marel, G.A. van der; Codée, J.D.C.; Overkleeft, H.S.
• Date: 2018-11-09
• Journal: European Journal of Organic Chemistry
• Volume: 2019
• Issue: 1
• Pages: 118 - 129
• DOI: doi:10.1002/ejoc.201801461
• Link: https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201801461