1241959-32-9Relevant academic research and scientific papers
A novel, concise and efficient protocol for non-natural piperidine compounds
Chavan, Subhash P.,Dumare, Nilesh B.,Pawar, Kailash P.
, p. 32594 - 32598 (2014/08/18)
Formal synthesis of l-altro-1-deoxynojirimycin, cis-3-hydroxypipecolic acid along with synthesis of (R)-piperidinol and a conceptually different advanced intermediate for non-natural piperidine alkaloids is reported from cis-butene-1,4-diol. The key react
Synthesis of eight 1-deoxynojirimycin isomers from a single chiral cyanohydrin
Van Den Nieuwendijk, Adrianus M.C.H.,Van Den Berg, Richard J.B H.N.,Ruben, Mark,Witte, Martin D.,Brussee, Johannes,Boot, Rolf G.,Van Der Marel, Gijsbert A.,Aerts, Johannes M.F.G.,Overkleeft, Herman S.
scheme or table, p. 3437 - 3446 (2012/08/27)
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.
Synthesis of l-altro-1-deoxynojirimycin, d-allo-1-deoxynojirimycin, and d-galacto-1-deoxynojirimycin from a single chiral cyanohydrin
Van Den Nieuwendijk, Adrianus M. C. H.,Ruben, Mark,Engelsma, Sander E.,Risseeuw, Martijn D. P.,Van Den Berg, Richard J.B.H.N.,Boot, Rolf G.,Aerts, Johannes M.,Brussee, Johannes,Van Der Marel, Gijs A.,Overkleeft, Herman S.
supporting information; experimental part, p. 3957 - 3959 (2010/11/19)
The chemoenzymatic synthesis of three 1-deoxynojirimycin-type iminosugars is reported. Key steps in the synthetic scheme include a Dibal reduction-transimination-sodium borohydride reduction cascade of reactions on an enantiomerically pure cyanohydrin, itself prepared employing almond hydroxynitrile lyase (paHNL) as the common precursor. Ensuing ring-closing metathesis and Upjohn dihydroxylation afford the target compounds.
