153957-98-3Relevant academic research and scientific papers
1,8-Diazabicyclo[5.4.0]undecene mediated transesterification of p-nitrophenyl phosphonates: A novel route to phosphono esters
Tawfik,Eshhar,Bentolila,Green
, p. 968 - 972 (2007/10/02)
DBU (1,8-diazabicyclo[5.4.0]undecene) was found to efficiently mediate the transesterification of p-nitrophenyl (PNP) phosphonates by various alcohols. The reactions of bis-PNP phosphonates in the presence of DBU, using both primary and secondary alcohols, phenols and amines, proceed rapidly and with high yield to afford the corresponding monoalkyl/aryl mono-PNP phosphonates as sole products (1, Scheme 2). The resulting monoalkyl/aryl mono-PNP phosphonates can be further reacted with a second alcohol to give the corresponding differently disubstituted phosphonates 3, or selectively hydrolysed to yield the monoalkyl/aryl phosphonic acids 2. We have applied this chemistry to the preparation of a series of phosphono ester transition state analogues 11a-e (Scheme 3) that were used as haptens for raising catalytic antibodies.
FROM PHOSPHONATES TO CATALYTIC ANTIBODIES. A NOVEL ROUTE TO PHOSPHONOESTER TRANSITION STATE ANALOGS AND HAPTENS
Tawfik, Dan S.,Eshhar, Zelig,Green, Bernard S.
, p. 123 - 126 (2007/10/02)
We present here a newly developed approach based on DBU catalyzed transesterification of bis-PNP-phosphonates, used for the preparation of phosphnoesters and their protein conjugates.These are being used, as transition state analogs, to elicit catalytic a
