55339-95-2

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 121-45-9 phosphorous acid trimethyl ester 
• 96-36-6 methyl phosphite 
• 501-52-0 3-Phenylpropionic acid 

Downstream Products

• 138479-07-9 (1-Hydroxy-1-nitromethyl-3-phenyl-propyl)-phosphonic acid dimethyl ester 
• 75089-92-8 (1-Methylene-3-phenyl-propyl)-phosphonic acid dimethyl ester 
• 162524-16-5 {1-[(E)-Hydroxyimino]-3-phenyl-propyl}-phosphonic acid dimethyl ester 
• 910548-97-9 [1-(Benzhydryl-amino)-3-phenyl-propyl]-phosphonic acid dimethyl ester 
• 89537-16-6 (+/-)-1-amino-3-phenylpropylphosphonic acid 

Relevant academic research and scientific papers

Multiple-step, one-pot synthesis of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates and their corresponding ethyl esters

The multiple-step, one-pot procedure for a series of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates, analogues of the natural, sulfur amino acid metabolite lanthionine ketimine (LK), its 5-ethyl ester (LKE) and 2-substituted LKEs is described. Initiating the synthesis with the Michaelis-Arbuzov preparation of α-ketophosphonates allows for a wide range of functional variation at the 2-position of the products. Nine new compounds were synthesized with overall yields range from 40 to 62%. In addition, the newly prepared 2-isopropyl-LK-P, 2-n-hexyl-LKE-P and 2-ethyl-LKE were shown to stimulate autophagy in cultured cells better than that of the parent compound, LKE.

A practical access to α-phosphonoenamides

Reaction of α-oximinophosphonates first with acetic anhydride then with iron powder and acetic acid at 50-60 °C results in the clean formation of an E-Z mixture of α-phosphonoenacetamides, which are immediate precursors to α-aminophosphonic acids.

New Synthesis and Hydroboration of Vinylphosphonates

The Arbuzov reaction of trimethyl and triethyl phosphites with acyl chlorides gave 1-oxoalkylphosphonates in 57-80percent yields.The Wittig reaction of the phosphonates with methylenetriphenylphosphorane gave vinylphosphonates in 25-59percent yields.Hydroboration of vinylphosphonates in oxolane gave 2-hydroxyethylphosphonates in 50-65percent yields.The procedure seems to be a good synthetic method to afford 1-alkyl-substituted 2-hydroxyethylphosphonates which have one more carbon atom than the starting 1-oxoalkylphosphonates.