79898-20-7

Basic information

• Product Name: (S)-α-methylbenzylammonium (2R,3S)-2,3-epoxy-3-phenylpropionate
• Synonyms: (S)-α-methylbenzylammonium (2R,3S)-2,3-epoxy-3-phenylpropionate
• CAS NO: 79898-20-7
• Molecular Weight: 285.343
• Mol File: 79898-20-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-α-methylbenzylammonium (2R,3S)-2,3-epoxy-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-α-methylbenzylammonium (2R,3S)-2,3-epoxy-3-phenylpropionate(79898-20-7)
• EPA Substance Registry System: (S)-α-methylbenzylammonium (2R,3S)-2,3-epoxy-3-phenylpropionate(79898-20-7)

Safety Data

• Hazardous Substances Data: 79898-20-7(Hazardous Substances Data)

Upstream product

• 121-39-1 ethyl 3-phenylglycidate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 19190-78-4 potassium trans-3-phenyloxiranecarboxylate 
• 1566-68-3 (2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 79898-19-4 (2R,3S)-3-phenyloxiranecarboxylic acid 
• 79869-88-8 N-<(2R,3R)-3-dimethylamino-2-hydroxy-3-phenylpropionyl>-(S)-α-methylbenzylamine 
• 79869-81-1 N-<(2R,3S)-2,3-epoxy-3-phenylpropionyl>-(S)-α-methylbenzylamine 

Relevant articles and documents

The preparation of optically active epineoclausenamide and enantiomeric separation of its racemate

We synthesized the optically active epineoclausenamide by utilizing chiral reagents, such as R-α-methylbenzylamine and S-α-methylbenzylamine, for the resolution of the intermediate (trans-3-phenyl-oxiranecarboxylic acid 12), followed by amide exchange, cy

Synthesis of the spermidine alkaloids (-)-(2R,3R)- and (-)-(2R,3S)-3-hydroxycelacinnine: Macrocyclization with oxirane-ring opening and inversion via cyclic sulfamidates

The two epimers (-)-1a and (-)-1b of the macrocyclic lactama kaloid 3-hydroxycelacinnine with the (2R,3R) and (2R,3S) absolute configurations, respectively, were synthesized by an alternative route involving macrocyclization with the regio- and stereoselective oxirane-ring opening by the terminal amino group (Schemes 2 and 6). Properly N-protected chiral trans-oxirane precursors provided (2R,3R)-macrocycles after a one-pot deprotection-macrocyclization step under moderate dilution (0.005-0.01M). The best yields (65-85%) were achieved with trifluoroacetyl protection. Macrocyclization of the corresponding cis-oxiranes was unsuccessful for steric reasons. Inversion at OH-C(3) via nucleophilic displacement of the cyclic sulfamidate derivative with NaNO2 led to (2R,3S)-macrocycles. The synthesized (-)-(2R,3S)-3-hydroxycelacinnine ((-)-1b) was identical to the natural alkaloid.