257296-68-7

Upstream product

• 647852-04-8 [(S)-2-Oxo-4-phenyl-3-(trityl-amino)-butyl]-phosphonic acid dimethyl ester 
• 647852-10-6 (E)-(S)-1,5-Diphenyl-4-(trityl-amino)-pent-1-en-3-one 
• 647852-19-5 (S)-2-Oxo-4-phenyl-3-(trityl-amino)-butyric acid methyl ester 
• 18598-80-6 methyl N-trityl-(S)-phenylalaninate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 63-91-2 L-phenylalanine 
• 647852-26-4 methyl (2S,3S)-3-(benzamido)-2-hydroxy-4-phenylbutanoate 
• 186581-53-3 diazomethane 
• 298206-12-9 (4S-trans)-4,5-dihydro-4-benzyl-2-phenyl-oxazoline-5-carboxylic acid 

Downstream Products

• 246523-10-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-4-phenylbutanoate 

Relevant academic research and scientific papers

A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

Practical synthetic routes to β-amino-α-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of β-amino-α- keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation.

Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0)

The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis and Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same π-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of β- amino-α-hydroxy acids 1 and γ-amino-β-hydroxy acids 2, conveniently protected as oxazoline.