125065-59-0Relevant academic research and scientific papers
An insight into the radical thiol/yne coupling: The emergence of arylalkyne-tagged sugars for the direct photoinduced glycosylation of cysteine-containing peptides
Minozzi, Matteo,Monesi, Alessandro,Nanni, Daniele,Spagnolo, Piero,Marchetti, Nicola,Massi, Alessandro
experimental part, p. 450 - 459 (2011/04/19)
An explorative study of the Thiol-Yne Coupling (TYC) reaction has been carried out using an aliphatic (1-octyne) and an aromatic alkyne (phenylacetylene) and two alkanethiols (methyl thioglycolate and N-acetyl-L-cysteine methyl ester). The outcomes of the TYC reactions strongly depend on the experimental conditions (e.g., temperature, solvent, and alkyne/thiol ratio), but these can be properly adjusted to achieve selective production of either mono-or bis-coupling products. With respect to 1-octyne, phenylacetylene undergoes notably easier radical hydrothiolation, further showing a notably higher aptitude for monohydrothiolation exclusive of bis-hydrothiolation. The overall findings were exploited in glycosylation of cysteine derivatives as well as of cysteine-containing peptides. A sugar featuring an arylacetylene moiety gave rise to a true click-reaction, that is, glycosylation of the tripeptide glutathione in its native form, by means of virtually equimolar amounts of reagents. This reaction was successfully applied, under physiological conditions, to a cysteine-containing nonapeptide with marked advantages over the analogous Thiol-Ene Coupling (TEC) derivatization. A TYC/TEC sequence affording bis-armed cysteine derivatives through dual functionalization of an alkynyl sugar was additionally devised.
THIOGLYCOLATES IN THE SYNTHESIS OF BIS(STYRYL)SULFONES
Reddy, M. V. Ramana,Reddy, S.,Reddy, D. Bhaskar,Padmavathi, V.
, p. 1101 - 1108 (2007/10/02)
E,Z-Bis(styryl)sulfones (6), have been prepared by the Knoevenagel condensation of Z-styrylsulfonylacetic acid (5) with araldehydes.The compound 5 was prepared by a novel route using thioglycolates and phenylacetylene.The configuration of 6 has been assig
