140170-77-0

Basic information

• Product Name: D-Valine, N-(2-hydroxy-1-phenylethyl)-N-(phenylmethyl)-, ethyl ester, (R)-
• CAS NO: 140170-77-0
• Molecular Formula: C22H29NO3
• Molecular Weight: 355.477
• Mol File: 140170-77-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: D-Valine, N-(2-hydroxy-1-phenylethyl)-N-(phenylmethyl)-, ethyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Valine, N-(2-hydroxy-1-phenylethyl)-N-(phenylmethyl)-, ethyl ester, (R)-(140170-77-0)
• EPA Substance Registry System: D-Valine, N-(2-hydroxy-1-phenylethyl)-N-(phenylmethyl)-, ethyl ester, (R)-(140170-77-0)

Safety Data

• Hazardous Substances Data: 140170-77-0(Hazardous Substances Data)

Upstream product

• 625-81-0 diisopropyl zinc 
• 144447-79-0 (2S,4R)-3-Benzyl-4-phenyl-oxazolidine-2-carboxylic acid ethyl ester 
• 14231-57-3 (R)-N-benzyl-2-phenylglycinol 

Downstream Products

• 3350-55-8 (R)-(-)-valine ethyl ester 

Relevant articles and documents

A New Chiral Glycine Synthon. Synthesis, X-Ray Structure of (-)-(2S,4R)-2-Ethoxycarbonyl-4-phenyl-1,3-oxazolidine and Diastereoselective Nucleophilic Ring Opening to (R)-Ethyl α-Amino Carboxylates.

Condensation of (R)-N-benzyl-2-phenylglycinol 1 with the methyl hemiacetal of ethyl glyoxylate leads to (2S,4R)-2-ethoxycarbonyl-4-phenyl-1,3-oxazolidine 2 as the major product, obtained as a pure enantiomer after column chromatography.Compound 2 is stereoselectively cleaved by dialkylzinc reagents, prepared from alkylmagnesium iodides and ZnCl2, with moderate to good d.e. (72-94 percent).These compounds, after separation by column chromatography and debenzylation by hydrogenolysis in the presence of 10percent Pd on carbon, lead to enantiomerically pure ethyl α-amino carboxylates with good chemical yields. Key words: Chiral Oxazolidines, alpha-amino Esters, Chiral Glycine Synthon, Ring Opening, Asymmetric Synthesis