198836-33-8

Basic information

• Product Name: methyl (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoate
• Synonyms: methyl (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoate
• CAS NO: 198836-33-8
• Molecular Weight: 316.335
• Mol File: 198836-33-8.mol

Chemical Properties

• CAS DataBase Reference: methyl (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoate(198836-33-8)
• EPA Substance Registry System: methyl (S)-3-methyl-2-(2-nitrophenylsulfonamido)butanoate(198836-33-8)

Safety Data

• Hazardous Substances Data: 198836-33-8(Hazardous Substances Data)

Upstream product

• 6306-52-1 L-valine methylester hydrochloride 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 4070-48-8 L-Valine methyl ester 

Downstream Products

• 198836-42-9 (S)-3-Methyl-2-[(2-nitro-benzenesulfonyl)-pent-4-enyl-amino]-butyric acid methyl ester 
• 1189547-59-8 methyl (S)-2-(2-aminophenylsulfonamido)-3-methylbutanoate 
• 1401065-78-8 methyl (S)-2-(2-acetamidophenylsulfonamido)-3-methylbutanoate 
• 40216-62-4 N-benzyl-L-valine methyl ester 
• 468773-46-8 7-isopropyl-1,3,3-methyl-6-(2-nitrobenzenesulfonyl)-octahydro-isoxazolo[3,4-c]pyridine 
• 468773-20-8 N-(4-methylpent-3-enyl)-N-(2-nitrobenzenesulfonyl)-(S)-valinol 
• 468773-21-9 N-(pent-4-enyl)-N-(2-nitrobenzenesulfonyl)-(S)-valinol 
• 468773-29-7 N-(4-methylpent-3-enyl)-N-(2-nitrobenzenesulfonyl)-(S)-valinal 
• 468773-30-0 N-(pent-4-enyl)-N-(2-nitrobenzenesulfonyl)-(S)-valinal 
• 468773-19-5 N-(but-3-enyl)-N-(2-nitrobenzenesulfonyl)-(S)-valinol 
• 468773-28-6 N-(but-3-enyl)-N-(2-nitrobenzenesulfonyl)-(S)-valinal 

Relevant articles and documents

Amino acid derived intramolecular 1,3-dipolar cycloadditions that form bridged medium ring systems with diastereoselective control

Intramolecular nitrone cycloadditions using amino acid precursors, generate aminohydroxyazepine and amino hydroxypiperidine templates. The cycloaddition reactions yield either a [4.3.0] fused system or in most cases a [4.2.1] bridged system. The [4.2.1] bridged system allows for the stereospecific preparation of 3-amino-5-hydroxyazepines while the [4.3.0] system allows for the preparation of 3-amino-5-hydroxymethyl piperidines.

Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.

Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes

The rhodium-catalyzed asymmetric ring opening reaction of oxabicyclic alkenes is shown to be an efficient method for synthesizing chiral heterocycles. We demonstrate that the pairwise combination of chiral catalyst with chiral amino-acid-derived pronucleophiles results in a stereodivergent synthesis of diastereomeric hydroxyesters. A favorable conformational preference induces the subsequent lactonization of one diastereomer leading to the highly enantioselective synthesis of oxazinones.

An unusual conformational similarity of two peptide folds featuring sulfonamide and carboxamide on the backbone

Two folded peptides featuring carboxamide and sulfonamide at the core of the peptide fold have been shown to possess almost similar conformational features, despite the well-known fact that carboxamides and sulfonamides have strikingly different hydrogen-

Microwave-accelerated cross-metathesis reactions of N-allyl amino acid substrates

Microwave heating has been utilised for the cross-metathesis reaction of N-allyl amino acid substrates to generate olefin homodimers. Remarkable acceleration of the cross-metathesis reaction (minutes compared to hours) over conventional reflux heating was

Investigation of the PDZ domain ligand binding site using chemically modified peptides

Several chemically modified analogues to a tightly binding ligand for the second PDZ domain of MAGI-3 were synthesized and evaluated for their ability to compete with native peptide ligands. N-methyl scanning of the ligand backbone amides revealed the energetically important hydrogen bonds between the ligand backbone and the PDZ domain. Analogues to the ligand's conserved threonine/serine(-2) residue, involved in a side chain to side chain hydrogen bond with a conserved histidine in the PDZ domain, revealed that the interaction is highly sensitive to the steric structure around the hydroxyl group of this residue. Analogues of the ligand carboxy terminus revealed that the full hydrogen bond network of the GLGF loop is important in ligand binding.

N-monoalkylation of α-amino acid esters under solid-liquid PTC conditions

N-(2-Nitrophenylsulfonyl)- (o-NBS-AA-OMe, 4) and N-(4- Nitrophenylsulfonyl)-α-amino acid methyl esters (p-NBSAA-OMe, 5) were N- alkylated with a variety of alkyl halides 6 under solid-liquid phase-transfer catalysis (SL-PTC) conditions, affording the alkylated products o-NBS-N-R2- AA-OMe 7 and p-NBS-N-R2-AA-OMe 8 in excellent yields without any detectable racemization.

A facile method for the N-alkylated of α-amino esters

Monoalkylation of the α-amino group of α-amino acid derivatives can be facilitated using 2 -and 4-nitrophenylsulfonamide intermediates. The nitrophenylsulfonamides of α-amino esters can be alkylated using an equimolar amount of carbonate base and a variety of alkyl bromides. Ready removal of the nitrophenylsulfonyl group is facilitated by S(N)Ar reaction between the N-alkylated sulfonamide and phenylthiolate to give the N-alkylated α-amino esters in good yield without racemisation of the chiral α-centres.