105838-14-0

Basic information

• Product Name: N-Boc-O-tosyl hydroxylamine
• Synonyms: N-Boc-O-tosyl hydroxylamine;Carbamic acid, [[(4-methylphenyl)sulfonyl]oxy]-, 1,1-dimethylethyl ester
• CAS NO: 105838-14-0
• Molecular Formula: C₁₂H₁₇NO₅S
• Molecular Weight: 287.34
• Mol File: 105838-14-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-Boc-O-tosyl hydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-O-tosyl hydroxylamine(105838-14-0)
• EPA Substance Registry System: N-Boc-O-tosyl hydroxylamine(105838-14-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 105838-14-0(Hazardous Substances Data)

Usage

Uses

Electrophilic N-amination of aryl and alkyl amines.

Upstream product

• 36016-38-3 tert-Butyl N-hydroxycarbamate 
• 98-59-9 p-toluenesulfonyl chloride 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 870-46-2 t-butoxycarbonylhydrazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 24608-52-4 tert-butyl chloroformate 

Downstream Products

• 134953-65-4 tert-Butoxycarbonylamino-phenyl-acetic acid isopropyl ester 
• 134981-68-3 (+/-)-diethyl 1-(tert-butoxycarbonylamino)phenylmethylphosphonate 
• 16066-84-5 N-(tert-butoxycarbonyl)methylamine 
• 134953-64-3 tert-butyl sec-butylcarbamate 
• 134953-66-5 3-(2-Amino-3-phenyl-propionyl)-oxazolidin-2-one 
• 3422-01-3 tert-butyl phenylcarbamate 
• 190059-40-6 [(S)-1-Benzyl-2-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 190059-42-8 [(S)-2-((3aS,8aR)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-2-oxo-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 91230-06-7 3--2-methylprop-1-ene 
• 1121-83-1 5,5-dimethyl-oxazolidin-2-one 
• 3712-40-1 tert-butyl cyclohexylcarbamate 
• 1266373-43-6 tert-butyl (S)-2-(3-(benzoyloxy)propyl)-2-formylaziridine-1-carboxylate 
• 1266373-38-9 tert-butyl (S)-2-benzyl-2-formylaziridine-1-carboxylate 
• 1254591-73-5 tert-butyl pivaloyl(N-tosyloxy)carbamate 

Relevant articles and documents

α-Nitrosostyrenes as Three-Atom Units for the (3+1) Cyclization Reaction: Facile Access to 2,3-Dihydrodiazete N-Oxides and Their Diversified Synthetic Conversions

An unprecedented (3+1) cyclization of α-nitrosostyrenes, generated in situ from α-bromooximes, and N-tosyloxycarbamates was developed, which enables the synthesis of a range of structurally unique and hitherto unexplored 2,3-dihydrodiazete N-oxides in mod

A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts

A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.

Novel quinoline derivative inhibitor

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An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation

The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza-ortho-quinone methides. Specifically, N-(tosyloxy)carbamates were used as an N1 synthon and bifunctional amino reagents for this transformation, which provides a metal-free, catalyst-free, and oxidant-free strategy to form nitrogen-nitrogen bonds. (Figure presented.).

FMOC PROTECTED (2S)-2-AMINO-8-[(1,1-DIMETHYLETHOXY)AMINO]-8-OXO-OCTANOIC ACID, (S)-2-AMINO-8-OXONONANOIC ACID AND (S)-2-AMINO-8-OXODECANOIC ACID FOR PEPTIDE SYNTHESIS

The invention discloses Fmoc protected (2S)-2-amino-8-[(1,1- dimethylethoxy)amino]-8-oxo-octanoic acid, (S)-2-amino-8- oxononanoic acid and (S)-2-amino-8-oxodecanoic acid for use in peptide synthesis, such as solid phase synthesis, as well as the peptide H3K27 (Ac-Lys-Ala-Ala-Arg-Aox-Ser-Ala-NH2) prepared from Fmoc protected (2S)-2-amino-8-[(1,1-dimethylethoxy)amino]-8-oxo-octanoic acid (Aox). These three exemplary compounds as well as their unprotected forms are claimed in the form of four generic formulae. The first of these four formulae is (formula (I)) where -NPro is a protected amino group, such as an amino group protected with a base-labile protecting group, -L- is alkylene, heteroalkylene, arylene or aralkylene, -X- is a covalent bond, -N(H) - or -N(RN)-, where -RN is alkyl, -R2 is hydrogen or alkyl, -R3 is alkyl, such as C2-10 alkyl, or heterocyclyl, and -LAA- and -R1 are as defined in the claims.

Enantioselective Aza-Heck Cyclizations of N-(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines

Pd(0)-systems modified with SPINOL-derived phosphoramidate ligands promote highly enantioselective aza-Heck cyclizations of alkenyl N-(tosyloxy)carbamates. The method provides versatile access to challenging N-heterocycles and represents the broadest scope enantioselective aza-Heck protocol developed to date.

Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions

A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.

ANTIVIRAL COMPOUNDS

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Enantioselective aziridination of cyclic enals facilitated by the fluorine-iminium ion Gauche effect

The enantioselective, organocatalytic aziridination of small, medium and macro-cyclic enals is reported using (S)-2-(fluorodiphenyl methyl)-pyrrolidine. Central to the reaction design is the reversible formation of a β-fluoroiminium ion intermediate, which is pre-organised on account of the fluorine-iminium ion gauche effect. This conformational effect positions the fluorine substituent synclinal-endo to the electropositive nitrogen centre thus benefiting from favourable stereoelectronic and electrostatic interactions (σC-H→σC-F*; F δ-···N+). Consequently, one of the shielding groups on the fluorine-bearing carbon atom is positioned above the π-system, forming the basis of an enantioinduction strategy. Treatment of this intermediate with a "nitrene" source furnished a series of novel, optically active aziridines (e.r. up to 99.5:0.5). Further derivatisation of the product aziridines gives facile access to various amino acid derivatives, including β-fluoroamino acids. Crystallographic analyses of both the aziridines and their derivatives are disclosed. Copyright

Osmium-catalyzed vicinal oxyamination of alkenes by N-(4- toluenesulfonyloxy)carbamates

N-(4-Toluenesulfonyloxy)carbamates based on a range of common amine protecting groups serve as preformed nitrogen sources in the intermolecular osmium-catalyzed oxyamination reaction of a variety of mono-, di-, and trisubstituted alkenes. The reactions occur with low catalyst loadings and good yields and afford high regioselectivity for unsymmetrically substituted alkenes.