78761-29-2Relevant articles and documents
On Amino Acid Antagonists,IV.-Separation and Determination of the Configurations of the Stereoisomeric N-Acetyl-2-(2'-cyclohexenyl)glycines
Santoso, Sentot,Kemmer, Thorsten,Trowitzsch, Wolfram
, p. 642 - 657 (2007/10/02)
The D-(+)-(1-phenylethyl)amides 5 as well as the D-(-)-O-acetyl-α-phenylglycinolamides 7 of the title compounds were separated on silica gel into the four diastereomeric compounds.All attempts failed to hydrolyze 5 and 7 to the corresponding acids.In contrast the diastereomeric D-(-)-N-acetyl-α-phenylglycinol esters 10 which were separated on silica gel were hydrolysed to the optically active acids 3a-d.The absolute configurations at C-2 in 3 were determined by correlation with the saturated glycine derivatives of known stereochemistry.The relative configurationsand hence the absolute configurations at C-1' in 3a-d were deduced from the NMR- and CD-spectra and were confirmed by X-ray analysis of 3a.Only the amino acid 3b with the (2S,1'R)-configuration exhibits biological activity.