53235-89-5

Upstream product

• 1660-94-2 Tetraethyl methylenediphosphonate 
• 104-88-1 4-chlorobenzaldehyde 
• 710-20-3 1-chloro-4-(2-nitropropenyl)benzene 

Downstream Products

• 1315613-59-2 (2S,3R)-methyl 2-amino-3-(4-chlorophenyl)-4,4-bis(diethoxyphosphoryl)butanoate 
• 53235-98-6 [2-(4-Chloro-phenyl)-1-(diethoxy-phosphoryl)-ethyl]-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

A Facile Cu(I)/TF-BiphamPhos-catalyzed asymmetric approach to unnatural α-amino acid derivatives containing gem-bisphosphonates

A novel catalytic asymmetric Michael addition of azomethine ylide with β-substituted alkylidene bisphosphates was realized in the presence of a chiral copper(I)/TF-BiphamPhos complex. The present system provides a unique and facile access to enantioenriched unnatural α-amino acid derivatives containing gem-bisphosphonates (gem-BPs) in high yields with excellent diastereoselectivities and enantioselectivities. Subsequent transformations lead to the expedient preparation of biologically active unnatural α-amino acid derivatives containing BPs and bisphosphonic acids without loss of diastereo- and enantiomeric excess.

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 62. REACTIONS OF METHYLENEBISPHOSPHONATE WITH α-NITROALKENES. A NOVEL SYNTHESIS OF ETHENYLIDENEBISPHOSPHONATES AND 2-ISOXAZOLINE-5,5-DIYLBISPHOSPHONATES

Reaction of methylenebisphosphonate with α-nitroalkenes followed by addition of trimethylchlorosilane leads to the formation of ethenylidenebisphosphonates and trimethylsilyl nitronate in almost quantitative yield.These two products, upon prolonged reaction at ambient temperature, provide 2-isoxazoline-5,5-diylbisphosphonates via regioselective 1,3-dipolar cycloaddition in high yield.Key words: Methylenebisphosphonate; α-nitroalkenes; ethenylidenebisphosphonate; 2-isoxazoline-5,5-diylbisphosphonate; 1,3-dipolar cycloaddition.