274681-89-9

Upstream product

• 195624-97-6 (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester 
• 60512-85-8 (E)-isopropyl cinnamate 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 442850-38-6 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxlic acid methylamide 
• 442850-31-9 (2S,3S)-2-acetylthio-3-benzoylamino-3-phenylpropanoic acid p-methoxybenzyl ester 
• 442850-39-7 (2S,3S)-2-acetylthio-3-benzoylamino-3-phenylpropanoic acid methylamide 
• 442850-30-8 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid p-methoxybenzyl ester 
• 442850-40-0 (S)-2-[((4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carbonyl)-amino]-propionic acid tert-butyl ester 
• 146848-91-1 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 
• 227962-26-7 (4S,5S)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.

Efficient syntheses and ring-opening reactions of trans- and cis-Oxazoline-5-carboxylates

cis- and trans-Oxazoline-5-carboxylates were synthesized effeciently from isopropyl trans-cinnamate utilizing the sharpless AA reaction. trans-Oxazoline was much more reactive than the cis-isomer toward ring opening reactions. From ab initio molecular calculation, the cis-isomer was predicted to be less reactive than the trans-isomer by 2.7 kcal/mol. Both syn and anti acetylthio ester and anti diamino ester were synthesized from these cis- and trans- oxazoline-5-carboxylates.