20806-43-3Relevant articles and documents
A new method for formacetal linkage formation: Protection of alcohols, phenols and carboxylic acids
Sawada, Daisuke,Ito, Yukishige
, p. 2501 - 2504 (2001)
A new formacetal linkage (ROCH2OR′) forming reaction was developed, which exploited a combination of sulfide (R′OCH2SR″) and CuBr2-Bu4NBr. This reaction proceeded to give high yields under neutral conditions and was applied to the protection of alcohols, phenols and carboxylic acids by several types of α-oxymethyl groups.
METHOD FOR PRODUCING CARBOXYLIC ACID AND ALCOHOL BY HYDROLYSIS OF ESTER
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Paragraph 0069; 0070, (2014/11/13)
As shown by the following formula (1), after methyl laurate (2 mmol) and water (8 mL) are added to an ammonium pyrosulfate catalyst (5 mol%), a hydrolysis reaction of methyl laurate is carried out by heating for 24 hours at 60°C while stirring is performed, so that lauric acid can be obtained with a yield of 86%.
N,N-diarylammonium pyrosulfate as a highly effective reverse micelle-type catalyst for hydrolysis of esters
Koshikari, Yoshiki,Sakakura, Akira,Ishihara, Kazuaki
experimental part, p. 3194 - 3197 (2012/07/31)
Reverse micelle-type N,N-diarylammonium pyrosulfate (3-5 mol %) efficiently catalyzes the hydrolysis of esters (up to 100 mmol scale) under organic solvent-free conditions. The present method is successfully applied to the hydrolysis of various esters without the decomposition of the base-sensitive moieties and without any loss of optical purity for α-heterosubstituted carboxylic acids.
A stereocontrolled synthesis of a new class of 3,4,5,6- tetrahydropyrimidine-based chiral amino acids
Zamri, Adel,Sirockin, Finton,Abdallah, Mohamed A.
, p. 5157 - 5170 (2007/10/03)
The stereocontrolled synthesis of seven 2-substituted-4-carboxy-3,4,5,6- tetrahydropyrimidines bearing either one chiral center at C-4 or two chiral centers at C-4 and C-8 was performed by condensation of (S)- or (R)- 2,4- diaminobutyric acid (Daba) with iminoethers derived from glycine, (S)- and (R)- serine, (S)- and (R)- tyrosine. Under the conditions reported, epimerization was always completely prevented at the C-4 center, whereas at the C-8 center, it was completely avoided in the case of tyrosine derivatives and considerably diminished for the serine derivatives.
6-Amino-2,4-lutidine carboxamides: α-aminoamide derivatives as systemic and topical inflammation inhibitors
Duflos, Muriel,Courant, Jacqueline,Le Baut, Guillaume,Grimaud, Nicole,Renard, Pierre,Manechez, Dominique,Caignard, Daniel-Henri
, p. 635 - 645 (2007/10/03)
The development of new potential anti-inflammatory compounds resulting from the incorporation of α-aminoacid residues into 6-amino-2,4-lutidine afforded (N-protected) aminoamides with interesting inhibitory activity. Out of 28 tested compounds, 10 (5a, 5b, 7d, 8a, 8b, 8d, 10a, 11b, 12a and 12b) exerted potent (> 90%) inhibition in the carrageenan foot edema (CFE) rat model after oral administration or 0.4 mmol kg-1. Except for Cbz-glycyl, Cbz-alanyl, Fmoc-valyl and Cbz-alanyl-glycyl derivatives (5a, 5b, 7d and 11b), N-deprotection afforded more active compounds. Introduction of a glycyl residue in the previously studied highly active 3-fluorobenzamide 2, which led to 10a, maintained potent peripheral edema inhibition but had a detrimental effect in the acute TPA-induced mouse ear-swelling model. Glycylglycinamide 12a, which had an ID50 of 9.0 mg kg-1 in the CFE test, appeared to be the most efficient compound tested in this new series of non-carboxylic nonsteroidal anti-inflammatory drugs. Glycinamide 8a, although less potent in the same assay (14.3 mg kg-1), exerted a significant inhihitory effect in acute and chronic ear-swelling tests after topical application of 3 mg/ear.
A Stereoselective Synthesis of threo-3-Hydroxyglutamic Acid
Dell'Uomo, Natalina,Giovanni, Maria C. Di,Misiti, Domenico,Zappia, Giovanni,Monache, Giuliano Delle
, p. 641 - 644 (2007/10/02)
The highly stereoselective iodocyclocarbamation of the chiral Z olefins 6 and 12, derived from the corresponding α-amino acid, yields threo-3-hydroxy-D- and -L-glutamic acid (1 and 2). - Key Words: Amino acids / Glutamic acids / Serine / Iodocyclocarbamation
Improved efficiency and selectivity in peptide synthesis: Use of triethylsilane as a carbocation scavenger in deprotection of t-butyl esters and t-butoxycarbonyl-protected sites
Mehta, Anita,Jaouhari, Rabih,Benson, Timothy J.,Douglas, Kenneth T.
, p. 5441 - 5444 (2007/10/02)
The use of triethylsilane as a carbocation scavenger in the presence of trifluoroacetic acid in dichloromethane leads to increased yields, decreased reaction times, simple work-up and improved selectivity for the deprotection of t-butyl ester and t-butoxycarbonyl sites in protected amino-acids and peptides in the presence of other acid-sensitive protecting groups such as the benzyloxycarbonyl, 9-fluorenylmethoxycarbonyl, O- and S-benzyl and t-butylthio groups.
A general and efficient route for chemical aminoacylation of transfer RNAs
Robertson, Stephanie A.,Ellman, Jonathan A.,Schultz, Peter G.
, p. 2722 - 2729 (2007/10/02)
A general and expedient procedure for the synthesis of aminoaeyl tRNA has been developed. The preparation of aminoacyl dCpA in one step and in high yield by reaction of the cyanomethyl active esters of N-protected α-amino with pdCpA is detailed. The preparation and photodeprotection of aminoacyl pdCpA derivatives containing nitroveratryl (NVOC) N-protected amino acids is also studied. The utility of the above methods for preparing aminoacyl tRNA was confirmed by enzymatically ligating NVOC-phenylalanyl pdCpA to tRNA-COH followed by photolysis to provide unprotected phenylalanyl tRNA. The phenylalanyl tRNA shown to be competent in an in vitro protein biosynthesis system. These protocols greatly simplify the use of chemically misacylated tRNAs in the synthesis of proteins containing unnatural ainino acids, as well as in studies of protein biosynthesis.
GLUTARAMIDE DIURETIC AGENTS
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, (2008/06/13)
A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5-or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.
