32563-40-9Relevant academic research and scientific papers
Electrochemical Dimethyl Sulfide-Mediated Esterification of Amino Acids
Li, Yongli,Wang, Huamin,Zhang, Heng,Lei, Aiwen
supporting information, p. 3023 - 3028 (2021/08/30)
Dimethyl sulfide-mediated electrochemical synthetic strategy for esterification of amino acids has been reported. A series of amino acids could react smoothly with alcohols, affording the desired esterification products with good efficiency. Importantly, the tolerance of peptides and gram-scale synthesis shed light on the utility of this protocol. Mechanistically, the dimethyl sulfide as a mediator plays an essential role in the transformation of amino acids.
Chiral tetraaryl-and tetraalkynylborates as chiral solvating agents for tetraalkylammonium salts
Tayama, Eiji,Sugawara, Takeshi
supporting information, p. 803 - 811 (2019/01/18)
The application of tetracarbon-substituted chiral borate sodium salts (NaBR*4) as NMR chiral solvating agents for various tetraalkylammonium salts (R4NX) has been successfully demonstrated. Ion exchange between R4NX and NaBR*4 proceeded in excellent yields and provided the corresponding dia-stereomeric salts (R4NBR*4). The ee values of the R4NX salts were determined by1H NMR analysis of R4NBR*4. Two types of chiral borates, tetraaryl-and tetraalkynylborates with optically active 1,1′-binaphthyl components were used. At the beginning of this research, we investigated the efficacy of a known chiral tetraar-ylborate developed by Pommerening et al. for R4NX. To expand the possibility of further structural design of the chiral borate, we designed chiral tetraalkynylborates as a new structure. Their synthesis and application are also described.
Chemoselective synthesis of carbamates using CO2 as carbon source
Riemer, Daniel,Hirapara, Pradipbhai,Das, Shoubhik
, p. 1916 - 1920 (2018/08/17)
Synthesis of carbamates directly from amines using CO2 as the carbon source is a straightforward and sustainable approach. Herein, we describe a highly effective and chemoselective methodology for the synthesis of carbamates at room temperature and atmosp
Bromodimethyl sulfonium bromide mediated rapid and facile protection of amines
Shailaja,Manjula,Vittal Rao
experimental part, p. 2073 - 2080 (2011/07/31)
A new clean protocol for protection of aryl and aliphatic amines with t-butoxycarbonyl (t-BOC) and benzyloxycarbonyl (Cbz) catalyzed by simple (bromodimethyl) sulfonium bromide has been developed. Rapid protection of amines in excellent yields in totally solvent-free conditions has been achieved. Copyright
New fast and practical method for the enantioselective synthesis of α-vinyl, α-alkyl quaternary α-amino acids
Di Giacomo, Marcello,Vinci, Valerio,Serra, Massimo,Colombo, Lino
, p. 247 - 257 (2008/09/19)
We describe a fast and practical enantioselective synthesis of (S)-N-Cbz-α-vinyl, phenylalanine, suitable for the preparation of different N-Cbz-α-vinyl aminoacids of both configurations. The new protocol exploits a Wittig reaction on highly enantiomeric enriched N-Cbz-α-formyl-α-alkyl amino esters, readily accessible from (l)-serine through a stereoselective alkylation of Seebach's oxazolidine, carried out with a significant improvement of the previously reported method. The synthetic scheme is suitable for gram scale preparation of the desired product with a 94% ee.
A mild and efficient chemoselective protection of amines as N-benzyloxycarbonyl derivatives in the presence of La(NO3)3·6H2O under solvent-free conditions
Chinni Mahesh,Narasimhulu,Srikanth Reddy,Suryakiran,Venkateswarlu
, p. 55 - 59 (2007/10/03)
A facile and versatile method for the chemoselective N-benzyloxycarbonylation of amines has been developed by treatment with benzyloxycarbonyl chloride (Cbz-Cl) in the presence of lanthanum(III) nitrate hexahydrate under solvent-free conditions. The metho
Efficient Access to Alanine Derivatives by 1,4-Additions of Potassium Trifluoro(organo)borates
Navarre, Laure,Darses, Sylvain,Genet, Jean-Pierre
, p. 69 - 73 (2007/10/03)
Potassium trifluoro(organo)borates, highly stable and easily prepared organoboran derivatives, were able to react with a great variety of dehydroamino esters. This reaction, catalyzed by rhodium complexes, allowed the formation of alanine derivatives bearing a great variety of amino protecting groups in good to high yields.
Benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate as N-protecting reagent
Hioki, Kazuhito,Fujiwara, Miho,Tani, Shohei,Kunishima, Munetaka
, p. 66 - 67 (2007/10/03)
A new active carbonate ester, benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate (Z-DMT), was prepared, and found to be a useful reagent for the introduction of benzyloxycarbonyl group into amines. Since Z-DMT is neither unstable nor irritating, it is practically useful.
A photochemical approach to phenylalanines and related compounds by alkylation of glycine
Knowles, Haydn S.,Hunt, Keith,Parsons, Andrew F.
, p. 8115 - 8124 (2007/10/03)
Phenylalanines can be prepared on UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, substituted toluenes and the photosensitiser benzophenone. These reactions, which lead to highly selective mono-alkylation at the α-position of glycines, involve coupling of captodative α-glycine radicals with benzyl radicals. This method can be used to selectively alkylate a variety of glycine derivatives using a range of substituted toluenes under neutral reaction conditions.
α-chymotrypsin-catalysed peptide synthesis via the kinetically controlled approach using activated esters as acyl donors in organic solvents with low water content: Incorporation of non-protein amino acids into peptides
Miyazawa, Toshifumi,Nakajo, Shin'ichi,Nishikawa, Miyako,Hamahara, Kazumi,Imagawa, Kiwamu,Ensatsu, Eiichi,Yanagihara, Ryoji,Yamada, Takashi
, p. 82 - 86 (2007/10/03)
The α-chymotrypsin-catalyzed peptide synthesis via the kinetically controlled approach using activated esters as acyl donors in orgnanic solvents with low water content was presented. The methyl esters of N-Z derivatives of racemic non-protein amino acids were chosen as carboxy components. They allowed the peptide-bond formation and optical resolution simultaneously to yield homochiral peptides. This method is useful for the incorporation of non-protein amino acids into peptides.
