29739-88-6

Usage

Uses

Used in Peptide Synthesis:
N-(p-Tosyl)-L-phenylalaninyl chloride is used as a building block for the synthesis of bioactive peptides. Its reactivity allows for the efficient incorporation of the phenylalanine amino acid into peptide sequences, which is crucial for the development of therapeutic peptides with specific biological activities.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, Tos-Phe-Cl is utilized as a reagent in the preparation of various chemical compounds and drugs. Its ability to introduce phenylalanine into complex molecular structures makes it a valuable tool in the synthesis of novel pharmaceuticals with potential therapeutic applications.
Used in Organic Chemistry Research:
N-(p-Tosyl)-L-phenylalaninyl chloride is employed as a versatile reagent in organic chemistry research. Its reactivity and the presence of the tosyl protecting group make it suitable for various synthetic transformations and the development of new organic compounds with potential applications in different fields.

InChI:InChI=1/C16H16ClNO3S/c1-12-7-9-14(10-8-12)22(20,21)18-15(16(17)19)11-13-5-3-2-4-6-13/h2-10,15,18H,11H2,1H3/t15-/m0/s1

Upstream product

• 13505-32-3 N-tosyl-(S)-phenylalanine 
• 98-59-9 p-toluenesulfonyl chloride 
• 63-91-2 L-phenylalanine 

Downstream Products

• 120402-85-9 N-tosyl-L-phenylalanyl-4-methylcoumaryl-7-amide 
• 99033-29-1 7-<(N-tosylphenylalanyl)amino>-4-chloro-3-methoxyisocoumarin 
• 88955-90-2 7-(N-tosyl-L-phenylalanyl)amino-4-nitrobenzo-2-oxa-1,3-diazole 
• 10119-00-3 tosyl-L-phenylalanyl diazomethane 
• 206441-84-1 3-tert-butoxycarbonylamino-2-methyl-6-[3-phenyl-2-(toluene-4-sulfonylamino)-propionylamino]-benzoic acid 2-trimethylsilanyl-ethyl ester 
• 1022223-94-4 (S)-N-(tosyl)phenylalanyl-(S)-O-phenyl-α-methylisoserine methyl ester 
• 157728-24-0 C₂₄H₂₆N₂O₃S 
• 1310868-17-7 C₂₄H₂₆N₂O₃S 
• 1267490-61-8 N-(p-toluenesulfonyl)-L-phenylalanine (R)-1-(4-methoxyphenyl)ethylamide 
• 1267490-54-9 (S)-N-(p-toluenesulfonyl)phenylalanine 3-methoxyphenylamide 
• 1267490-53-8 (S)-N-(p-toluenesulfonyl)phenylalanine 2-methoxyphenylamide 

Relevant academic research and scientific papers

Synthesis and structural studies of new N-(p-toluenesulfonyl)amino acid o-phenolamides

The synthesis and structural studies of N-(p-Toluenesulfonyl)amino acid o-phenolamides was discussed. The structure and conformation of these amides were established by NMR spectroscopy and x-ray crystallography. Variable temperature experiments showed th

Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling

An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp3)-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp3)-H bonds were aminated, and various functional groups were tolerated.

Metal-Free N–H/C–H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α-Amino Acids

We have developed a method for the synthesis of dihydroquinoxalinones via intramolecular N–H/C–H coupling using hypervalent iodine. The starting materials were prepared from inexpensive and readily available aniline and amino acid derivatives. Various functional groups were tolerated to give multisubstituted dihydroquinoxalinones in moderate to excellent yields. The chirality of the amino acid was transferred to the desired target compound without a loss of enantiomeric excess. Preliminary mechanistic studies indicated that the reaction proceeds via an ionic mechanism.

Oxazoline derivatives tagged with tosylated amino acids as recyclable organocatalysts for enantioselective allylation of aldehydes

A series of amino acid-based oxazoline compounds have been prepared and successfully applied to the enantioselective allylation reaction of aldehydes. The fine-tuning of the structure of the oxazolines led to (S,S)-4 as an efficient organocatalyst which gave homoallyl alcohols in good yield (up to 90%) and excellent ee (up to 99%) for a wide range of substrates including aromatic, hetero-aromatic and α,β-unsaturated aldehydes. The chiral organocatalyst was synthesized in three easy steps with an overall 88% yield and successfully recycled for up to three cycles. On the basis of the experimental observations and NMR studies, a probable mechanism was proposed for this reaction.

Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity

A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%)

Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole

A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.

C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine-an intermediate for APN inhibitor

Recyclable chiral amide-based organocatalyst 5 efficiently catalyzed asymmetric Strecker reaction of various aromatic and aliphatic N-benzhydrylimines with ethyl cyanoformate as cyanide source at -10 °C to give a high yield (95%) of α-aminonitriles with excellent chiral induction (ee, up to 99%) with the added advantage of recyclability. Based on experimental observations a probable mechanism was proposed for this reaction. This protocol with catalyst 5 was extended for the synthesis of (R)-phenylalanine and pharmaceutically important drug intermediate (R)-3-phenylpropane-1,2-diamine in high yield with high enantioselectivity.

Enantiomers of all-cis-5-(4-bromophenyl)-4-tert-butoxycarbonyl-2- methoxycarbonylpyrrolidine: Preparative HPLC separation and acylative kinetic resolution of the racemate

The fundamental possibility of acylative kinetic resolution of racemic heterocyclic amines was demonstrated by the example of all-cis-5-(4-bromophenyl) -4-tert-butoxycarbonyl-2-methoxycarbonylpyrrolidine. Individual enantiomers (ee >99%) were obtained in

Modular amino acids-based chiral ligands for copper-catalyzed enantioselective conjugation addition of diethylzinc to cyclic enones

New amino acid-based modular chiral ligands were readily synthesized and used to catalyze the asymmetric conjugate addition of Et2Zn to various cyclic enones in the presence of a variety of copper sources. Moderately high ee of up to 72% were o

Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation

New sulfonamide-derived hydroxamic acids 7-11 have been developed as chiral ligands for the V-catalysed asymmetric epoxidation, showing high reactivity at subzero temperatures and moderate to good enantioselectivity. The strong accelerating effect exhibited by the ligands of this type can be attributed to the sulfonamide functionality. A range of cinnamyl type allylic alcohols were epoxidised with up to 74% ee. The Royal Society of Chemistry 2005.