Premium
Synthesis of Glycosylated 1‐Deoxynojirimycins Starting from Natural and Synthetic Disaccharides
Author(s) -
Liu Bing,
van Mechelen Jeanine,
van den Berg Richard J. B. H. N.,
van den Nieuwendijk Adrianus M. C. H.,
Aerts Johannes M. F. G.,
van der Marel Gijsbert A.,
Codée Jeroen D. C.,
Overkleeft Herman S.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801461
Subject(s) - chemistry , reductive amination , bioorganic chemistry , amination , combinatorial chemistry , organic chemistry , catalysis , enzyme
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.