106889-84-3Relevant academic research and scientific papers
A Nitrone Dipolar Cycloaddition Strategy toward an Enantioselective Synthesis of Massadine
Cannon, Jeffrey S.
, p. 3883 - 3887 (2018)
An enantioselective route to the C,D-bicycle of massadine is reported. Enantiopure intermediates were generated by a single stereoselective reduction using the Corey-Bakshi-Shibata reagent. This initial stereoinduction was translated into the five contigu
GAS TREATING SOLUTIONS CONTAINING IMIDAZOLE-AMINE COMPOUNDS AND METHODS OF MAKING THE SAME
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Paragraph 0203, (2021/12/03)
Systems comprising a composition where an imidazole is tethered to an amine and a solvent are described herein. Methods of their preparation and use are also described herein. The methods of using the systems include the reduction of volatile compounds from gas streams and a liquid stream.
AZACARBAZOLE BTK INHIBITORS
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Page/Page column 57; 58, (2016/10/31)
The present invention provides Bruton's Tyrosine Kinase (Btk) inhibitor compounds according to Formula (I), or pharmaceutically acceptable salts thereof, wherein CH, R1, R1a, R1b, R2, R3, and the subscripts m1, m2, p, q, and t are as set forth herein. The present invention also provides pharmaceutical compositions comprising these compounds and their use in therapy. In particular, the present invention relates to the use of Btk inhibitor compounds of Formula (I) in the treatment of Btk mediated disorders.
DAST mediated preparation of β-fluoro-α-aminophosphonates
Ka?mierczak, Marcin,Koroniak, Henryk
experimental part, p. 23 - 27 (2012/06/30)
Herein, we report a new and convenient method for the synthesis of β-fluoro-α-aminophosphonates starting from naturally occurring l-amino acids. A key step in the synthetic protocol involves nucleophilic fluorination of N,N-dibenzylated-β-amino alcohols with diethylaminosulfur trifluoride (DAST).
Towards convenient precursors for α-phosphonylated aziridinium ions
Piotrowska, Dorota G.,Wroblewski, Andrzej E.
experimental part, p. 998 - 1016 (2009/12/03)
Mixtures of the respective 2-(N,N-dibenzylamino)-1-chloro- and 1-(N,N-dibenzylamino)-2-chlorophosphonates were obtained after mesylation of dimethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-methylbutylphosphonate and diethyl (1R,2S)-2-(N,N-dibenzylamino)-1-hydroxy-3-phenylpropylphosphonate with mesyl chloride in the presence of tetraethylammonium chloride. These mixtures are considered as useful precursors to-phosphonylated aziridinium ions.
Glucosamine conjugates bearing N,N,O-donors: Potential imaging agents utilizing the [M(CO)3]+ core (M = Re, Tc)
Bowen, Meryn L.,Lim, Nathaniel C.,Ewart, Charles B.,Misri, Ripen,Ferreira, Cara L.,Haefeli, Urs,Adam, Michael J.,Orvig, Chris
experimental part, p. 9216 - 9227 (2010/02/15)
The design rationale, synthesis and radiolabeling evaluation of four glucosamine conjugated ligands for the [99mTc(CO)3] + core is described. The capability to bind the tricarbonyl core is initially demonstrated using the cold surrogate [Re(CO)3] +. The four compounds are competent chelates in binding [ 99mTc(CO)3]+ as labeling studies show, with yields ranging from 79 to 96% and the resulting complexes showing stability in the presence of competing chelates for 24 h at 37 °C. The rhenium complexes were tested for hexokinase-catalysed phosphorylation, and the technetium complexes were tested for GLUT-1 mediated cell uptake - they showed a small amount of uptake but it was not glucose dependent, suggesting that it was not via the GLUT-1 transporters.
Total synthesis of (-)-7-epicylindrospermopsin, a toxic metabolite of the freshwater cyanobacterium Aphanizomenon ovalisporum, and assignment of its absolute configuration
White, James D.,Hansen, Joshua D.
, p. 1963 - 1977 (2007/10/03)
(Chemical Equation Presented) The Z and E nitrones 38 and 39 from condensation of aldehyde 20 with hydroxylamine 36 underwent intramolecular dipolar cycloaddition to give the substituted 1-aza-7-oxobicyclo[2.2.1] heptanes 40 and 41 in a ratio of 2:1, respectively. Reductive N-O bond cleavage of 40 followed by carbonylation gave cyclic urea 47 in which inversion of the secondary alcohol was effected via an oxidation-reduction sequence. After conversion of the p-bromobenzyl ether 50 to azide 54, activation of the cyclic urea as its O-methylisourea and reduction of the azide led to spontaneous cyclization to afford the tricyclic nucleus 59 of cylindrospermopsin. Global deprotection, including hydrolysis of the 2,4-dimethyoxypyrimidine appendage to a uracil, and then monosulfation of the resultant diol 60 afforded a substance identical with natural (-)-7-epicylindrospermopsin (1). The asymmetric synthesis of (-)-7-epicylindrospermopsin defines its absolute configuration as 7S,8R,10S,12S,13R,14S.
Asymmetric synthesis of L-[4-13C]lysine by alkylation of oxazinone derivative as a chiral glycine equivalent
Takatori, Kazuhiko,Hayashi, Akira,Kajiwara, Masahiro
, p. 787 - 795 (2007/10/03)
L-[4-13C]Lysine (2) was synthesized from sodium [2- 13C]acetate (3) and Dellaria's oxazinone 1 as a chiral glycine equivalent. Wittig reaction of the glycinal 7 and 13C-labeled phosphonium ylide 5, prepared from sodium [2-13C]acetate (3), gave the α, β-unsaturated ester 8. The ester 8 was converted to the allylic bromide 10. Alkylation of the oxazinone 1 with 10 proceeded with high diastereoselectivity. Ethanolysis, hydrogenation of the double bond with diimide, removal of the chiral auxiliary, and hydrolysis gave L-[4- 13C]lysine (2). Copyright
Asymmetric nucleophilic a-amino-acylation with metalated chiral amino nitriles: Enantioselective synthesis of 3-substituted 5-amino4-oxo-esters via asymmetric Michael addition
Enders, Dieter,Shilvock, John P.,Raabe, Gerhard
, p. 1617 - 1619 (2007/10/03)
Highly stereoselective conjugate addition of an enantiopure metalated β-amino substituted amino nitrile to a,β-unsaturated esters, with subsequent silver nitrate induced hydrolysis of the amino nitrile adducts affords 3-substituted 5-amino-4-oxo-esters wi
Enantioselective synthesis of differently protected 1,2-diamines via α-alkylation of dibenzylaminoacetaldehyde SAMP-hydrazone
Enders, Dieter,Schiffers, Robert
, p. 53 - 58 (2007/10/03)
Chiral, unsymmetrically and differently protected 1,2-diamines 4 were prepared in moderate to good overall yields and with high asymmetric inductions (ee = 91-99%) by α-alkylation of N,N-dibenzylaminoacetaldehyde SAMP-hydrazone (S)-2 with subsequent oxidative cleavage to the corresponding α-aminonitriles, reduction to the diamines, and protection of the latter.
