o-Mesitylenesulfonylhydroxylamine - CAS 36016-40-7
Catalog number: 36016-40-7
Category: Intermediates
Molecular Formula:
Molecular Weight:
O-(MESITYLSULFONYL)HYDROXYLAMINE; O-mesitylenesulphonylhydroxylamine; O-Mesitylenesulfonylhydroxylamine; 2-[(Aminooxy)sulfonyl]-1,3,5-trimethylbenzene; O-(2,4,6-Trimethylphenyl)sulfonylhydroxylamine; N-hydroxy-2,4,6-trimethylbenzenesulfonamide
Boiling Point:
381ºC at 760 mmHg
Melting Point:
Canonical SMILES:
1.Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: versatile and switchable access to functionalized proteins.
Bernardes GJ1, Chalker JM, Errey JC, Davis BG. J Am Chem Soc. 2008 Apr 16;130(15):5052-3. doi: 10.1021/ja800800p. Epub 2008 Mar 22.
An efficient and robust oxidative elimination of cysteine to dehydroalanine has been discovered. The reaction is induced by O-mesitylenesulfonylhydroxylamine (MSH) and is compatible with methionine. The key elimination has been executed on protein surfaces and allows ready access to different post-translationally modified proteins through conjugate addition of sulfur nucleophiles to dehydroalanine. Treatment of the resulting thioether with MSH results in regeneration of dehydroalanine, allowing a "functional switch" by subsequent addition of a different thiol.
2.Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine.
Cho GY1, Okamura H, Bolm C. J Org Chem. 2005 Mar 18;70(6):2346-9.
[reaction: see text] The asymmetric synthesis and chemical modification of p-bromophenyl methyl sulfoximine (2) is described. Starting from p-bromophenyl menthyl sulfinate (5), enantiopure 2 can be obtained in a short reaction sequence involving a well-established substitution reaction followed by stereospecific imination with O-mesitylenesulfonylhydroxylamine (MSH). Palladium-catalyzed Buchwald/Hartwig, Suzuki, and Stille coupling reactions allow a broad variation of the sulfoximine aryl group, which is otherwise difficult to achieve. The incorporation of a p-morpholino-substituted derivative into a pseudotripeptide demonstrates the applicability of the novel sulfoximine derivatives.
3.Highly efficient synthesis of O-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides.
Legault C1, Charette AB. J Org Chem. 2003 Sep 5;68(18):7119-22.
An efficient two-step synthesis of O-(2,4-dinitrophenyl)hydroxylamine is described along with a comparison of its aminating efficiency with O-mesitylenesulfonylhydroxylamine (MSH). It was used in an expedient N-amination/benzoylation procedure involving various substituted pyridines, leading to polysubstituted N-benzoyliminopyridinium ylides, and the scope of its amination power was studied.
4.N-[(N-halogenoacyl)imino]acenaphthene-quinoxalines as potential antitumoral agents.
Boido A1, Vazzana I, Sparatore F. Farmaco. 1994 Feb;49(2):97-104.
Applying a reaction formerly studied by the Authors between acenaphthenequinone and N1-(2-amino)phenyl-N2-acylhydrazines, a group of N-[(N-alpha- and beta- halogenoacyl)imino]acenaphthenequinoxalines were obtained. On account of the reactivity of the halogen atom, they are potentially interesting as antitumoral agents. In contrast with the beta-chloropropionyl derivative, the alpha-halogenoacyl derivatives were formed in low yields and with the simultaneous loss of the whole halogenoacylimino group. Thus, an alternative synthetic route was set up, consisting in the N-imination of acenaphthenequinoxalines by means of O-mesitylenesulfonylhydroxylamine, followed by acylation of the intermediate N-iminoacenaphthenequinoxalines. The National Cancer Institute of Bethesda evaluated the activity against lymphocytic leukemia P 388 on some of the numerous compounds now described. Only the N-chloroacetyliminoacenaphthenequinoxaline exhibited, at the dose of 50 mg/Kg i.
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CAS 36016-40-7 o-Mesitylenesulfonylhydroxylamine

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