3693-95-6Relevant academic research and scientific papers
Pd/BIPHEPHOS is an Efficient Catalyst for the Pd-Catalyzed S-Allylation of Thiols with High n-Selectivity
Schlatzer, Thomas,Schr?der, Hilmar,Trobe, Melanie,Lembacher-Fadum, Christian,Stangl, Simon,Schl?gl, Christoph,Weber, Hansj?rg,Breinbauer, Rolf
supporting information, p. 331 - 336 (2019/11/16)
The Pd-catalyzed S-allylation of thiols with stable allylcarbonate and allylacetate reagents offers several advantages over established reactions for the formation of thioethers. We could demonstrate that Pd/BIPHEPHOS is a catalyst system which allows the transition metal-catalyzed S-allylation of thiols with excellent n-regioselectivity. Mechanistic studies showed that this reaction is reversible under the applied reaction conditions. The excellent functional group tolerance of this transformation was demonstrated with a broad variety of thiol nucleophiles (18 examples) and allyl substrates (9 examples), and could even be applied for the late-stage diversification of cephalosporins, which might find application in the synthesis of new antibiotics. (Figure presented.).
[[(tert-Butyl)dimethylsilyl]oxy]-methylGroup for sulfur protection
Wang, Lihong,Clive, Derrick L. J.
, p. 1734 - 1737 (2011/06/09)
Aromatic and aliphatic thiols can be protected by reaction with t-BuMe 2SiOCH2Cl in DMF in the presence of a base (2,6-lutidine or proton sponge); the resulting t-BuMe2SiOCH2SR or t-BuMe2SiOCH2SAr are deprotected by sequential treatment with Bu4NF and I2 to give symmetrical disulfides. Another mode of deprotection involves reaction with a sulfenyl chloride; this process gives an unsymmetrical disulfide and was examined with Me(CH2) 11SCH2OSiMe2Bu-t and three sulfenyl chlorides.
Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues
Bhat, Ramakrishna G.,Porhiel, Emmanuel,Saravanan, Vadivelu,Chandrasekaran, Srinivasan
, p. 5251 - 5253 (2007/10/03)
Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.
Process for S-Aryl cysteine
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Example 2, (2008/06/13)
The present invention provides methods for preparing S-aryl cysteines in enantiomeric excess of greater than about 96%. Specifically, the present invention provides enantioselective methods for preparing S-aryl cysteines starting from cystine, cysteine or
One pot conversion of alcohols to disulfides mediated by benzyltriethylammonium tetrathiomolybdate
Sinha, Surajit,Ilankumaran,Chandrasekaran
, p. 14769 - 14776 (2007/10/03)
A one pot conversion of alcohols to disulfides in good yields via the activation of a hydroxyl group with DCC or P(NMe2)3 / CCl4 followed by treatment with benzyltriethylammonium tetrathiomolybdate is reported.
A new efficient method for S-CH2-S bond formation and its application to a djenkolic acid-containing cyclic enkephalin analog
Ueki, Masaaki,Ikeo, Takayoshi,Hokari, Kumiko,Nakamura, Keiko,Saeki, Akihiko,Komatsu, Hiroshi
, p. 829 - 838 (2007/10/03)
An efficient methylene insertion reaction to construct an S-CH2-S bridge between two cysteine residues occurred when the thiol-protecting dimethylphosphinothioyl (Mpt) group of Z-Cys(Mpt)-OMe was removed with tetrabutylammonium fluoride hydrate in CH2Cl2. The thiol-free form gave similar results, albeit the yields were somewhat lower. In both cases, the best yields were obtained using 2 molar amounts of the reagent. Higher amounts of the reagent reduced the yield because of dehydroalanine formation. In the case of penicillamine, the thiol-free form was better in reactivity than the S-Mpt form, which required double the amount of the reagent to give the same yield. The reaction was successfully used in a synthesis of a cyclic enkephalin analog with the S-CH2-S bridge.
Conjugate addition of ammo acid side chains to alkynones and alkynoic acid derivatives
Crisp, Geoffrey T.,Millan, Michael J.
, p. 637 - 648 (2007/10/03)
Suitably protected amino acids were used to investigate the Michael addition of the sulfanyl group of cysteine, the hydroxyl group of serine and the ε-amino group of lysine to a conjugated alkynone, alkynoic ester and alkynoic amide. The expected heterosu
Electrophilic Sulfur Transfer Reactions in Organic Synthesis. Preparation of a Diastereomer of the Key Macrocyclic Component of Griseoviridin
Liu, Li,Tanke, Robin S.,Miller, Marvin J.
, p. 5332 - 5337 (2007/10/02)
The utility of electrophilic sulfur transfer reactions was demonstrated by the synthesis of a diastereomer of the key macrocyclic cycteine containing component of griseoviridin.The key step involved direct reaction at the sulfur of N-(carbobenzyloxy)-S-ph
The Synthesis of Substituted thio>acetic Acids
Woulfe, Steven R.,Miller, Marvin J.
, p. 3133 - 3139 (2007/10/02)
The synthesis of substituted thio>acetic acids (6, thiamazins) is described.Various substituted 3(S)-(acylamino)-2-azetidinones were sulfenylated with tert-butyl (phtalimidothio)acetate.Deprotection of the tert-butyl ester with trifluoroacetic acid provided the title compounds.In sharp contrast to their oxygen analogues (oxamazins), the thiamazins were devoid of biological activity.
