86124-72-3Relevant academic research and scientific papers
Solid phase synthesis of bicyclic pyrrolidines
Quadrelli, Paolo
, (2021/11/17)
The preparation of bicyclic pyrrolidines, stable and easy to isolate, is performed through both classical solution chemistry and on solid support. A new linker strategy is presented based on the concept of REM resin approach. Starting from a suitably derivatized Wang's resin, the linker can be REgenerated after cleavage of the product and functionalized to start a new synthetic cycle via a Michael reaction. In the present work a vinyl sulfone supported on a Wang's resin is able to undergo a Michael reaction with an amino acid derivative; the obtained adduct serves as a precursor for azomethine ylide generation, which is conveniently trapped with N-methyl-maleimide. The results are presented and discussed in the light of the experimental conditions applied as well as the method chosen for the cleavage of the product and resin regeneration.
ARYL-VINYLSULFONE--REAGENTIEN ZUM SCHUTZ UND NACHWEIS VON THIOLFUNKTIONEN
Horner, L.,Lindel, H.
, p. 1 - 8 (2007/10/02)
Aryl vinyl sulfones selectively react with thiol groups to acid-stable compounds which easily are cleaved by mild bases to thiol compounds.Ester and amide groups are not attacked under these conditions.Therefore, these compounds are good protecting groups or labels in peptide chemistry.The following aryl vinyl sulfones were investigated: phenyl vinyl sulfone 1, p-carbethoxyphenyl vinyl sulfone 15 and the fluorescent 5-dimethylaminonaphthyl 1-vinyl sulfone 5 and 5-methoxynaphthyl-1 vinyl sulfone 10.The last two compounds are very useful reagents for the quantitative determination of SH-groups in polypeptides such as enzymes.
