459216-72-9

Upstream product

• 100-52-7 benzaldehyde 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 459216-68-3 (1S,2S,3S)-2-(Dimethoxy-phosphoryl)-3-phenyl-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid methyl ester 
• 459217-15-3 (1S,2S,3S)-2-(Dimethoxy-phosphoryl)-3-phenyl-2-((S)-toluene-4-sulfinyl)-cyclopropanecarboxylic acid ethyl ester 
• 459216-90-1 E-(S)-(1-dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide 

Downstream Products

• 1418016-88-2 (2S,1'S,2'R,3'S,S_S)-[(N-p-toluenesulfinyl)-2-amino]-2-[2'-dimethoxyphosphoryl-3'-phenyl]cyclopropylethanenitrile 
• 1418016-95-1 C₂₀H₂₃N₂O₄PS 
• 1418016-87-1 (1S,2R,3S,S_S)-N-(2-Dimethoxyphosphoryl)-(3-phenyl)cyclopropylmethylidene-p-toluenesulfinamide 
• 1418016-86-0 (1R,2S,3S)-dimethoxyphosphoryl-2-formyl-3-phenylcyclopropane 
• 1418016-85-9 (1R,2S,3S)-1-dimethoxyphosphoryl-2-hydroxymethyl-3-phenylcyclopropane 
• 459216-81-0 ((1R,2R,3R)-2-tert-Butoxycarbonylamino-3-phenyl-cyclopropyl)-phosphonic acid dimethyl ester 
• 459216-77-4 (1S,2R,3S)-2-(Dimethoxy-phosphoryl)-3-phenyl-cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

Asymmetric synthesis of conformationally constrained L-AP4 analogues using chiral sulfinyl auxiliary

Constrained L-AP4 analogues, (2S,1′R,2′S)- and (2S,1′S,2′R)-2-(2′-phosphonocyclopropyl) glycines as well as their phenyl analogues (2S,1′S,2′R,3′S)-2-(2′-phosphono- 3′-phenylcyclopropyl) glycine (PPCG-1) and (2S,1′R,2′S, 3′R)-2-(2′-phosphono-3′-phenylcyclopropyl) glycine (PPCG-2) were synthesized. The stereogenic centers in cyclopropane ring were formed under sulfinyl group control, in asymmetric cyclopropanation of enantiomerically pure a-phosphoryl vinyl sulfoxides. The sulfinimine-mediated asymmetric Strecker reaction allowed to introduce amino acid moiety.

Asymmetric cyclopropanation of chiral (1-dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide: A new synthesis of enantiomerically pure 2-amino-3-phenyl-1-cyclopropane-phosphonic acid - A constrained analog of phaclofen

E-(S)-(1-Dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide 3 was found to undergo cyclopropanation with sulfur ylides [dimethyl(oxo)sulfonium methylide, diphenyl sulfonium isopropylide and ethyl (dimethylsulfuranylidene)acetate (EDSA)] in a highly diastereoselective manner. The major diastereomer obtained in the reaction of E-(S)-3 with EDSA was converted into enantiopure (2R)-amino-(3R)-phenyl-(1R)-cyclopropane-phosphonic acid, a constrained analog of the GABAB antagonist, phaclofen.