160252-94-8Relevant academic research and scientific papers
Amphipathic sulfonamidobenzamides mimicking small antimicrobial marine natural products; investigation of antibacterial and anti-biofilm activity against antibiotic resistant clinical isolates
Igumnova, Elizaveta M.,Mishchenko, Ekaterina,Haug, Tor,Blencke, Hans-Matti,Sollid, Johanna U. Ericson,Fredheim, Elizabeth G. Aarag,Lauksund, Silje,Stensv?g, Klara,Str?m, Morten B.
, p. 4930 - 4941 (2018/09/11)
There is an urgent need for novel antimicrobial agents to address the threat of bacterial resistance to modern society. We have used a structural motif found in antimicrobial marine hit compounds as a basis for synthesizing a library of antimicrobial sulf
N-Fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI): A sterically demanding electrophilic fluorinating reagent for enantioselective fluorination
Yasui, Hiroyuki,Yamamoto, Takeshi,Ishimaru, Takehisa,Fukuzumi, Takeo,Tokunaga, Etsuko,Akikazu, Kakehi,Shiro, Motoo,Shibata, Norio
scheme or table, p. 222 - 225 (2011/04/26)
We disclose here a novel electrophilic fluorinating reagent, N-fluoro-(3,5-di-tert-butyl-4-methoxy)benzenesulfonimide (NFBSI) as a sterically demanding analogue of popular fluorinating reagent, N-fluorobenzenesulfonmide (NFSI). NFBSI improves the enantios
Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones
Mase, Nobuyuki,Watanabe, Yoshihiko,Ueno, Yoshio,Toru, Takeshi
, p. 7794 - 7800 (2007/10/03)
The diastereoselectivity of intermolecular β-addition of alkyl radicals to 2-(arylsulfinyl)-2-cycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of 2-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the 1H NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the β-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.
Factors Influencing the Acid Lability of Substituted Arylsulphonyl Arginine Protecting Groups
Ali, Syed Safdar,Echner, Hartmut,Khan, Khalid Mohammed,Schroeder, Christoph,Hasan, Mashooda,et al.
, p. 1425 - 1433 (2007/10/02)
The kinetics of hydrolysis of new, NG-protected 2,4,6-triisopropylbenzene-sulphonyl (6), 4-methoxy-3,5-di-tert-butylbenzenesulphonyl (12) and phenanthrene-3-sulphonyl (17) Fmoc derivatives of L-arginine (1) in comparison with commercially available Fmoc-Arg(Mtr)-OH (Mtr = 4-methoxy-2,3,6-trimethyl-benzenesulphonyl (2)) are studied.The acid lability of the arylsulphonyl group is decreasing as follows Mtr > Tip > Mtbs > Phen.The effect of electron-donating alkyl groups as substituents in increasing the acid lability of the arylsulphonyl residue seems to be in the order of methyl > isopropyl > tert-butyl, while the effect of extended delocalization does not appreciably increase the acid lability. - Keywords: 2,4,6-Triisopropylbenzenesulphonyl (Tip), 4-methoxy-3,5-di-tert-butylbenzenesulphonyl (Mtbs), Phenanthrene-3-sulphonyl (Phen) Residues
