298208-76-1

Basic information

• Product Name: (4S-trans)-4,5-dihydro-4-benzyl-2-phenyloxazoline-5-acetic Acid
• Synonyms: (4S-trans)-4,5-dihydro-4-benzyl-2-phenyloxazoline-5-acetic Acid
• CAS NO: 298208-76-1
• Molecular Weight: 295.338
• Mol File: 298208-76-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (4S-trans)-4,5-dihydro-4-benzyl-2-phenyloxazoline-5-acetic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4S-trans)-4,5-dihydro-4-benzyl-2-phenyloxazoline-5-acetic Acid(298208-76-1)
• EPA Substance Registry System: (4S-trans)-4,5-dihydro-4-benzyl-2-phenyloxazoline-5-acetic Acid(298208-76-1)

Safety Data

• Hazardous Substances Data: 298208-76-1(Hazardous Substances Data)

Upstream product

• 257296-71-2 (4S-trans)-4,5-dihydro-4-benzyl-5-(2-hydroxyethyl)-2-phenyloxazoline 
• 257296-53-0 N-((2S)-5-acetoxy-1-phenyl-3-butenyl)benzamide 
• 303766-36-1 N-((E)-(S)-1-Benzyl-4-hydroxy-but-2-enyl)-benzamide 
• 298208-80-7 (E)-(S)-4-Amino-5-phenyl-pent-2-en-1-ol 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 72155-45-4 Boc-L-phenylalaninal 
• 124818-94-6 ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 
• 124818-93-5 (4S)-4-(N-tert-butoxycarbonyl)amino-5-phenyl-2-penten-1-ol 
• 208935-28-8 (4S-trans)-4,5-dihydro-4-benzyl-2-phenyl-5-vinyloxazoline 
• 35593-57-8 (S)-N-(1-oxo-3-phenylpropan-2-yl)benzamide 
• 5267-65-2 (S)-N-(1-hydroxy-3-phenylpropan-2-yl)benzamide 

Downstream Products

• 125356-66-3 (+)-preussin 
• 210964-94-6 (+)-(2S,3S,5R)-2-benzyl-3-hydroxy-5-nonylpyrrolidine 
• 317322-37-5 1-((4S,5S)-4-benzyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-undecan-2-one 
• 317322-36-4 2-((4S,5S)-4-benzyl-2-phenyl-4,5-dihydro-oxazol-5-yl)-N-methoxy-N-methyl-acetamide 

Relevant articles and documents

Process for the preparation of oxazoline compound

The present invention relates to a process for the preparation of an oxazoline compound which is easily chemically converted to a beta-amino-alpha-hydroxy acid or a gamma-amino-beta-hydroxy acid. The method comprises producing a compound of the following formula (4) using alpha -amino acid. The produced compound (4) is subjected to an intramolecular cyclization to produce an oxazoline compound of the following formula (3). The oxazoline compound (3) is oxidized at a vinyl group with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (1) which is easily chemically converted to a beta-amino-alpha-hydroxy acid. Alternatively, the oxazoline compound (3) may also be treated with 9-borabiclo[3.3.1]nonane such that a hydroxy group is introduced into the end of the vinyl group of the oxazoline compound(3). The introduced end hydroxy group is oxidized with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (2) which is easily chemically converted to a gamma-amino-hydroxy acid.

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.