Asymmetric synthesis of (2R,3S)-4-halo-3-benzyloxy-2-(N-methoxycarbonyl-N-benzylamino)butyronitriles as precursors for the synthesis of β-hydroxy-α-amino acids

Add time:07/14/2019    Source:sciencedirect.com

(2R,3S)-4-Halo-3-benzyloxy-2-(N-methoxycarbonyl-N-benzylamino)butyronitriles have been prepared through an efficient three-step sequence from (2R,3S)-2-benzylamino-3-benzyloxy-4-(tert-butyldimethylsilyloxy)butyronitrile, which is readily available in diastereomerically pure form by a Strecker-type reaction of the N-benzylimine, derived from selectively protected (R)-glyceraldehyde, and trimethylsilyl cyanide. These compounds enable the facile synthesis of chiral β-hydroxy-α-amino acids containing virtually any nucleophile capable of substituting the γ-halogen atom. As an illustration of their synthetic potential, the 4-bromo derivative has been successfully converted into (1R,2R)-2-benzyloxy-1-(N-methoxycarbonyl-N-benzylamino)cyclopropanecarboxamide, which is a new conformationally restricted serine analogue, in two steps: base-induced cyclisation and subsequent hydrolysis of the nitrile group.

We also recommend Trading Suppliers and Manufacturers of 4-amino-N-(2-{[4-(benzyloxy)-3-chloro-5-methoxybenzyl]amino}ethyl)-1,2,5-oxadiazole-3-carboxamide (cas 893602-91-0). Pls Click Website Link as below: cas 893602-91-0 suppliers

Prev:Spectroscopic analysis and charge transfer interaction studies of 4-benzyloxy-2-nitroaniline insecticide: A density functional theoretical approach
Next:Separation of heparin on SEPHAROSE CL-4B (cas 61970-08-9) in the presence of high concentrations of ammonium sulphate)