184537-69-7Relevant academic research and scientific papers
Remarkable diastereomeric rearrangement of an α-acyloxy β-ketosulfide to an α-acyloxy thioester: A novel approach to the synthesis of optically active (2S,3S) β-amino α-hydroxy acids
Suzuki, Takayuki,Honda, Yutaka,Izawa, Kunisuke,Williams, Robert M.
, p. 7317 - 7323 (2007/10/03)
A novel and efficient synthetic method is described for (2S,3S)-3-amino-2-hydroxy-4-phenyl butyric acid derivatives, which are useful intermediates of enzyme inhibitors. This involves a Pummerer rearrangement of a β-ketosulfoxide derived from L-phenylalanine followed by highly stereoselective acyl migration. From these studies, it appears that nitrogen-protecting groups exert a substantial influence over stereoselectivity. The mechanism of the rearrangement is discussed. β-Amino α-hydroxy carboxylic acids are important pharmaceutical intermediates, and this method may provide a versatile synthesis from various amino acids in a few steps.
An efficient synthesis of N-protected threo (2R,3S)-3-amino-1,2-epoxy phenylbutane
Suzuki, Takayuki,Honda, Yutaka,Izawa, Kunisuke
, p. 5811 - 5814 (2007/10/03)
A precise and versatile method was developed for the synthesis of threo amino epoxide derivatives, which are useful intermediates for protease inhibitors. It involves the diastereoselective reduction of the carbonyl group of γ-N,N-dibenzyl amino α-hydroxy β-keto sulfide prepared from an amino acid, and its subsequent stereospecific conversion to an amino epoxide via acetoxy halogenation in high yield.
Process for producing norstatin derivatives
-
, (2008/06/13)
This invention to provide a process for producing an optically active threo-phenylnorstatin derivative which does not require a toxic cyanating agent or a costly reagent, or a complicated procedure, and can be practiced on a commercial scale. This inventi
