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Synthesis of L-altro-1-deoxynojirimycin, D-allo-1-deoxynojirimycin, and D-galacto-1-deoxynojirimycin From a Single Chiral Cyanohydrin

Adrianus M C H van den Nieuwendijk, Mark Ruben, Sander E Engelsma, Martijn D P Risseeuw, Richard J B H N van den Berg, Rolf G Boot, Johannes M Aerts, Johannes Brussee, Gijs A van der Marel, Herman S Overkleeft

Org Lett. 2010 Sep 3;12(17):3957-9.

PMID: 20690611

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP37468329 ALLO-1 ALLO-1 37468-32-9 Price
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