196214-22-9

Basic information

• Product Name: (S)-methyl 2-(2,4-dinitrophenylsulfonamido)-3-phenylpropanoate
• Synonyms: (S)-methyl 2-(2,4-dinitrophenylsulfonamido)-3-phenylpropanoate
• CAS NO: 196214-22-9
• Molecular Weight: 409.376
• Mol File: 196214-22-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-methyl 2-(2,4-dinitrophenylsulfonamido)-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 2-(2,4-dinitrophenylsulfonamido)-3-phenylpropanoate(196214-22-9)
• EPA Substance Registry System: (S)-methyl 2-(2,4-dinitrophenylsulfonamido)-3-phenylpropanoate(196214-22-9)

Safety Data

• Hazardous Substances Data: 196214-22-9(Hazardous Substances Data)

Upstream product

• 1656-44-6 2,4-dinitrobenzenesulfonyl chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 20902-47-0 N-tert-butoxycarbonyl-L-valyl-L-phenylalanine methyl ester 
• 192057-94-6 2-(tert-butoxycarbonylamino)isobutyryl-L-phenylalanine methyl ester 
• 1146929-53-4 C₂₄H₂₉ClN₂O₅S 
• 1154041-21-0 (Nα-benzyloxycarbonyl-Nγ-(β-D-glucopyranosyl)-L-asparaginyl)-L-phenylalanine methyl ester 
• 1154041-22-1 (Nα-benzyloxycarbonyl-Nγ-{4-(β-D-glucopyranosyl)-β-D-glucopyranosyl}-L-asparaginyl)-L-phenylalanine methyl ester 
• 1154041-23-2 (Nα-benzyloxycarbonyl-Nγ-{4-(α-D-glucopyranosyl)-β-D-glucopyranosyl}-L-asparaginyl)-L-phenylalanine methyl ester 
• 1154041-00-5 C₂₀H₂₈N₂O₉ 
• 1154041-02-7 methyl N-[(methyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside)-2-ylsuccinamyl]-L-phenylalaninate 
• 1197342-59-8 CNS-L-Phe-L-Phe-OMe 
• 1197342-74-7 FNS-L-Val-L-Val-L-Phe-OMe 
• 1197342-60-1 ENS-L-Ala-L-Phe-L-Phe-OMe 
• 3618-96-0 (S)-N-acetylphenylalanine 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Relevant articles and documents

Amino acid and peptide synthesis and functionalization by the reaction of thioacids with 2,4-dinitrobenzenesulfonamides

(Formula Presented) Readily prepared amino thioacids react at room temperature in DMF in the presence of cesium carbonate with 2,4- dinitrobenzenesulfonamides to give amides. When the sulfonamide is derived from an amino acid the method results in peptide bond formation, whereas the use of carbohydrate derived sulfonamides gives neoglycoconjugates.

One-pot syntheses of dissymmetric diamides based on the chemistry of cyclic monothioanhydrides. Scope and limitations and application to the synthesis of glycodipeptides

(Chemical Equation Presented) Opening cyclic monothioanhydrides by amines provides a convenient entry into amido thioacids that can be trapped in situ by 2,4-dinitrobenzenesulfonamides, by electron-deficient azides, or by amines in the presence of Sanger's reagent leading, in each case, to dissymmetric diamides in what can be considered a one-pot, three-component coupling sequence. The use of monothiomaleic anhydride and bifunctional nucleophiles such as amino thiols provides access to heterocyclic amides. The low reactivity of cyclic monothioanhydrides toward alcohols enables the use of methanol as solvent and obviates the need for the protection of alcohols in the various reaction components. Reaction of N-benzyloxycarbonyl-L-aspartic monothioanhydride with unprotected glycosyl amines, followed by capture of the thioacid intermediate with N-sulfonyl amino acid derivatives results in a three-component convergent synthesis of glycosylated peptides.