Synthesis of Eight 1-Deoxynojirimycin Isomers from a Single Chiral Cyanohydrin

Adrianus M. C. H. van den Nieuwendijk, Richard J. B. H. N. van den Berg, Mark Ruben, Martin D. Witte, Johannes Brussee, Rolf G. Boot, Gijsbert A. van der Marel, Johannes M. F. G. Aerts, Herman S. Overkleeft

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Abstract

Eight configurational 1-deoxynojirimycin isomers have been synthesized starting from a chiral cyanohydrin as the common precursor. The cyanohydrin chiral pool building block is easily accessible in large quantities by using almond hydroxynitrile lyase as the chiral catalyst in condensing hydrogen cyanide and crotonaldehyde. Our work complements the large body of literature on the synthesis of 1-deoxynojirimycin derivatives with the distinguishing feature that eight stereoisomers of this important class of glycosidase inhibitors can be derived from a common precursor in an efficient manner
Original languageEnglish
Pages (from-to)3437-3446
JournalEuropean Journal of Organic Chemistry
Volume2012
Issue number18
DOIs
Publication statusPublished - 2012

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