393588-04-0

Basic information

• Product Name: 1,2-Propanediol, 3-phenyl-3-[[(1R)-1-phenylethyl](phenylmethyl)amino]-, (2R,3R)-
• CAS NO: 393588-04-0
• Molecular Formula: C24H27NO2
• Molecular Weight: 361.484
• Mol File: 393588-04-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,2-Propanediol, 3-phenyl-3-[[(1R)-1-phenylethyl](phenylmethyl)amino]-, (2R,3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Propanediol, 3-phenyl-3-[[(1R)-1-phenylethyl](phenylmethyl)amino]-, (2R,3R)-(393588-04-0)
• EPA Substance Registry System: 1,2-Propanediol, 3-phenyl-3-[[(1R)-1-phenylethyl](phenylmethyl)amino]-, (2R,3R)-(393588-04-0)

Safety Data

• Hazardous Substances Data: 393588-04-0(Hazardous Substances Data)

Upstream product

• 38235-77-7 (R)-N-benzyl-1-phenylethylamine 
• 14990-09-1 tert-butyl cinnamate 
• 151671-03-3 tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate 

Downstream Products

• 25705-52-6 (R)-phenylglycine hydrochloride 
• 38329-34-9 (S)-α-amino-α-phenylacetic acid hydrochloride 
• 393588-07-3 (2R,αR)-2-phenyl-2-(N-benzyl-N-α-methylbenzylamino)ethanal 
• 393588-13-1 (2R,αR)-2-phenyl-2-(N-benzyl-N-α-methylbenzylamino)ethanoic acid 

Relevant articles and documents

Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

An efficient protocol for the transformation of homochiral α-hydroxy-β-amino esters to their α-amino carbonyl components is presented. Diastereoselective conjugate addition of lithium (R)-N-benzyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters and subsequent enolate hydroxylation with (1R)-(-)-(camphorsulfonyl)oxaziridine, followed by LiAlH4 reduction produces homochiral 3-amino 1,2-diols. Subsequent oxidative cleavage with H5IO6 provides N-benzyl-N-α-methylbenzyl protected α-amino aldehydes (96-98% d.e.) and ketones (88% d.e.). Further oxidation of the α-amino aldehydes with sodium chlorite and Pd-catalysed hydrogenation provides α-amino acids in 94-98% e.e.