19190-78-4

Basic information

• Product Name: Oxiranecarboxylic acid, 3-phenyl-, potassium salt, (2R,3S)-rel-
• CAS NO: 19190-78-4
• Molecular Formula: C9H8O3.K
• Molecular Weight: 202.251
• Mol File: 19190-78-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Oxiranecarboxylic acid, 3-phenyl-, potassium salt, (2R,3S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarboxylic acid, 3-phenyl-, potassium salt, (2R,3S)-rel-(19190-78-4)
• EPA Substance Registry System: Oxiranecarboxylic acid, 3-phenyl-, potassium salt, (2R,3S)-rel-(19190-78-4)

Safety Data

• Hazardous Substances Data: 19190-78-4(Hazardous Substances Data)

Upstream product

• 121-39-1 ethyl 3-phenylglycidate 
• 121-39-1 ethyl cis-3-phenylglycidate 

Downstream Products

• 76527-41-8 (2S,3R)-3-Phenyl-oxirane-2-carbonyl chloride 
• 133534-75-5 (RS,RS) ethyl<(1-methoxy-2-(2-ethoxyphenoxy)-2-phenyl)ethyl>imidoate hydrochloride 
• 133534-38-0 (RS,SR) 1-ethyl-2-<1-methoxy-2-(2-ethoxyphenoxy)-2-phenyl>ethyl-1H-imidazole 
• 133534-34-6 (RS,SR) 1-ethyl-2-<1-methoxy-2-(2-ethoxyphenoxy)-2-phenyl>ethyl-4,5-dihydro-1H-imidazole 
• 133534-36-8 (RS,SR) 2-<1-methoxy-2-(2-ethoxyphenoxy)-2-phenyl>ethyl-1H-imidazole 
• 133534-56-2 (RS,RS) methyl 2-hydroxy-3-(2-ethoxyphenoxy)-3-benzenepropanoate 
• 133534-69-7 (RS,RS) 2-methoxy-3-(2-ethoxyphenoxy)-3-benzenepropanamide 
• 133534-63-1 (RS,SR) 2-methoxy-3-(2-ethoxyphenoxy)-benzenepropanenitrile 
• 134460-49-4 (RS,RS) methyl 2-methoxy-3-phenoxy-3-benzenepropanoate 
• 133534-52-8 (RS,RS) methyl 2-hydroxy-3-phenoxy-3-benzenepropanoate 
• 133534-67-5 (RS,RS) 2-methoxy-3-phenoxy-3-benzenepropanamide 
• 133534-48-2 (RS,SR) 2-<1-methoxy-2-(2-ethoxyphenoxy)-2-phenyl>ethyl-4,5-dihydro-1H-imidazole hydrochloride 
• 133534-75-5 (RS,SR) ethyl<(1-methoxy-2-(2-ethoxyphenoxy)-2-phenyl)ethyl>imidoate hydrochloride 
• 133534-38-0 (RS,RS) 1-ethyl-2-<1-methoxy-2-(2-ethoxyphenoxy)-2-phenyl>ethyl-1H-imidazole 

Relevant articles and documents

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.