Cas no 86117-53-5 (N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine)

N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine is a chiral sulfonamide derivative of D-phenylalanine, characterized by its tosyl (p-toluenesulfonyl) protecting group. This compound is primarily utilized in peptide synthesis and asymmetric organic transformations, where its sterically hindered structure and enantiomeric purity enhance selectivity in coupling reactions. The sulfonyl group improves stability and facilitates purification, while the D-configuration of phenylalanine makes it valuable for studying enzyme specificity or designing bioactive peptides. Its crystalline solid form ensures consistent handling and storage. The compound is particularly useful in medicinal chemistry research, where precise stereochemical control is critical for modulating biological activity.
N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine structure
86117-53-5 structure
Product Name:N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine
CAS No:86117-53-5
MF:C16H17NO4S
MW:319.37548327446
MDL:MFCD15071654
CID:1843591
PubChem ID:686492
Update Time:2025-06-08

N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine Chemical and Physical Properties

Names and Identifiers

    • N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine
    • (R)-2-(4-methylphenylsulfonamido)-3-phenylpropanoic acid
    • (2R)-2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoic acid
    • N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine (ACI)
    • N-p-Tosyl-D-phenylalanine
    • N-tosyl-r-phenylalanine
    • Tosyl-D-phenylalanine
    • D-Phenylalanine, N-[(4-methylphenyl)sulfonyl]-
    • NTE288EK7H
    • DS-12202
    • AKOS027338543
    • 86117-53-5
    • DB-336217
    • N-p-toluenesulfonyl-D-phenylalanine
    • CS-0169311
    • (2R)-2-{[(4-methylphenyl)sulfonyl]amino}-3-phenylpropanoic acid
    • (R)-2-(4-methylphenylsulfonamido)-3-phenylpropanoicacid
    • MFCD15071654
    • SCHEMBL1203540
    • (2R)-2-(4-METHYLBENZENESULFONAMIDO)-3-PHENYLPROPANOIC ACID
    • N-TOSYL-D-PHENYLALANINE
    • DTXSID30350707
    • MDL: MFCD15071654
    • Inchi: 1S/C16H17NO4S/c1-12-7-9-14(10-8-12)22(20,21)17-15(16(18)19)11-13-5-3-2-4-6-13/h2-10,15,17H,11H2,1H3,(H,18,19)/t15-/m1/s1
    • InChI Key: CGRCVIZBNRUWLY-OAHLLOKOSA-N
    • SMILES: S(C1C=CC(C)=CC=1)(=O)(=O)N[C@@H](C(=O)O)CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 319.08782920g/mol
  • Monoisotopic Mass: 319.08782920g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 6
  • Complexity: 457
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.8
  • Topological Polar Surface Area: 91.8?2

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N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Diethyl ether ,  Water ;  10 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water
Reference
Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity
Ghosh, Debashis; et al, Organic & Biomolecular Chemistry, 2013, 11(21), 3451-3460

Production Method 2

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Tempo ,  Cupric nitrate ,  Potassium bisulfate Solvents: 1,2-Dichloroethane ;  24 h, rt
Reference
Copper-catalyzed aerobic oxidation of primary alcohols to carboxylic acids
Yu, Yibo; et al, Chemical Communications (Cambridge, 2023, 59(35), 5281-5284

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Diethyl ether ,  Water ;  rt; 6 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  < 7 °C
Reference
Multi-step application of immobilized reagents and scavengers: A total synthesis of epothilone C
Storer, R. Ian; et al, Chemistry - A European Journal, 2004, 10(10), 2529-2547

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Diethyl ether ,  Water ;  overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, rt
Reference
Allylation of Aldehydes and Imines: Promoted by Reusable Polymer-Supported Sulfonamide of N-Glycine
Li, Gui-Long; et al, Organic Letters, 2006, 8(4), 633-636

Production Method 5

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  25 °C; overnight, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
Reference
Carbonic anhydrase inhibitors: Design, synthesis, kinetic, docking and molecular dynamics analysis of novel glycine and phenylalanine sulfonamide derivatives
Fidan, Ismail; et al, Bioorganic & Medicinal Chemistry, 2015, 23(23), 7353-7358

Production Method 6

Reaction Conditions
1.1 Reagents: (3R,5R,6S,8R)-1,3,4,5,6,7,8,10-Octahydro-5,6-bis(2-hydroxyphenyl)-3,8-bis(phenyl… Solvents: Chloroform-d ;  rt
Reference
Synthesis of macrocycles and their application as chiral solvating agents in the enantiomeric recognition of carboxylic acids and α-amino acid derivatives
Guo, Shengnan; et al, Tetrahedron: Asymmetry, 2013, 24(8), 480-491

N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine Raw materials

N-[(4-Methylphenyl)sulfonyl]-D-phenylalanine Preparation Products

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