88347-91-5Relevant academic research and scientific papers
Dealkenylative Thiylation of C(sp3)-C(sp2) Bonds
Smaligo, Andrew J.,Kwon, Ohyun
supporting information, p. 8592 - 8597 (2019/10/14)
Carbon-carbon bond fragmentations are useful methods for the functionalization of molecules. The value of such cleavage events is maximized when paired with subsequent bond formation. Herein we report a protocol for the cleavage of an alkene C(sp3)-C(sp2) bond, followed by the formation of a new C(sp3)-S bond. This reaction is performed in nonanhydrous solvent and open to the air, employs common starting materials, and can be used to rapidly diversify natural products.
Preparation of arylmercapturic acids by S-arylation of N,N′- diacetylcystine
Krouzelka, Jan,Linhart, Igor
experimental part, p. 6336 - 6340 (2011/03/19)
A simple convenient method has been developed for the preparation of N-acetyl-S-arylcysteines based on the Chan-Lam-Evans arylation of N,N′-diacetylcystine dimethyl ester with arylboronic acids and used to synthesize a series of arylmercapturic acids. Unlike copper-mediated N-arylation, the S-arylation of neither cysteine nor cystine derivatives proceeded satisfactorily in the presence of air. Wiley-VCH Verlag GmbH & Co. KGaA.
Methyl mercapturate synthesis: An efficient, convenient and simple method
Cossec, Benoit,Cosnier, Frederic,Burgart, Manuella
experimental part, p. 2394 - 2407 (2009/04/11)
A safe and simple method for methyl S-arylmercapturate synthesis is described. Thirteen such compounds, to be used afterwards in metabolism studies, have been obtained with yields ranging from 71 to 99.6%. These compounds were obtained using a sulfa-Michael addition and synthesized by adding the corresponding thiophenols to a mixture composed of methyl 2-acetamidoacrylate (MAA), potassium carbonate and a phase transfer catalyst, Aliquat 336. MAA, the initial synthon, was itself isolated in quasi quantitative yield following a fully described synthesis.
Approaches toward the total synthesis of the nine-membered thio-lactone core of griseoviridin
Moreau, Xavier,Campagne, Jean-Marc
, p. 5346 - 5350 (2007/10/03)
Three different approaches toward the synthesis of the macrocyclic thiolactone core of griseoviridin have been studied. Intramolecular palladium-catalyzed thiol coupling and esterification (carboxylate activation) have led to the formation of unexpected rearranged products. An intermolecular palladium-catalyzed thiol/vinyl iodide coupling followed by an esterification (alcohol activation) ultimately led to the nine-membered core of griseoviridin.
S-substituted 2-azido-3-mercapto-propionic acid ester and process for its production and use
-
, (2008/06/13)
The subject matter of the invention are S-substituted 2-azido-3-mercapto-propionic acid esters of the general formula STR1 in which R1 is a methyl or ethyl group and R2 is an unsubstituted or substituted alkyl group, a cycloalkyl group, an unsubstituted or substituted aromatic or heteroaromatic group or a benzyl group, and a process for their production by reaction of a methyl or ethyl ester of 2-chloroacrylic acid with a corresponding thiol to form an S-substituted 2-chloro-3-mercapto-propionic acid ester and subsequently exchanging the chlorine atom with an azido group as well as use of the compounds of formula (I) as intermediate products in the production of D,L-cysteine or derivatives of D,L-cysteine.
Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis
Beckwith,Easton
, p. 3995 - 4001 (2007/10/02)
The Cu-catalysed reaction of the substituted 3-phenylthiopropianamide with di-t-butyl peroxide gives the β-lactam via oxidative cyclisation of the α-thioalkyl radical. Similar reactions of the propionamides with t-butyl perbenzoate give benzoates which can be readily converted into the β-lactams, but neither β-lactams nor benzoates can be obtained from the thiazepines. Dimethyl disulfide is benzoyloxylated on treatment with t-butyl perbenzoate. The relevance of these results to penicillin biosynthesis is discussed.
