Cas no 89813-47-8 (2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate)

2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate structure
89813-47-8 structure
Product Name:2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
CAS No:89813-47-8
MF:C17H23NO5
MW:321.368225336075
MDL:MFCD00076979
CID:588418
PubChem ID:11902907
Update Time:2024-10-26

2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate Chemical and Physical Properties

Names and Identifiers

    • 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl)2-(phenylmethyl) ester, (2S,4R)-
    • BOC-HYP-OBZL
    • Boc-O-Hyp-OBzl
    • Boc-trans-L-4-hydroxyproline benzyl ester
    • N-Boc-trans-4-hydroxy-L-proline benzyl ester
    • (2S,4R)-4-Hydroxy-1,2-Pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) 2-(phenylmethyl) ester
    • 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) 2-(phenylmethyl) ester, (2S-trans)- (ZCI)
    • 1-(1,1-Dimethylethyl) 2-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (ACI)
    • N-(tert-Butoxycarbonyl)-4-hydroxyproline benzyl ester
    • 2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
    • 89813-47-8
    • XH0429
    • MFCD00076979
    • BEIPCYKSYYZEJH-KGLIPLIRSA-N
    • SCHEMBL1150829
    • (2s,4r)-2-benzyl 1-t-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate
    • AS-49203
    • 2-O-benzyl 1-O-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
    • 2-Benzyl 1-(tert-butyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
    • (2S,4R)-2-Benzyl1-tert-butyl4-hydroxypyrrolidine-1,2-dicarboxylate
    • CS-0159086
    • AKOS015895923
    • 2-Benzyl 1-(tert-butyl) (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate
    • AKOS015836548
    • FD21790
    • Benzyl (4R)-1-Boc-4-hydroxy-L-prolinate
    • BocHypOBn
    • Boc-Hyp-OBn
    • (2S,4R)-2-Benzyl 1-tert-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate
    • MDL: MFCD00076979
    • Inchi: 1S/C17H23NO5/c1-17(2,3)23-16(21)18-10-13(19)9-14(18)15(20)22-11-12-7-5-4-6-8-12/h4-8,13-14,19H,9-11H2,1-3H3/t13-,14+/m1/s1
    • InChI Key: BEIPCYKSYYZEJH-KGLIPLIRSA-N
    • SMILES: C(N1C[C@H](O)C[C@H]1C(=O)OCC1C=CC=CC=1)(=O)OC(C)(C)C

Computed Properties

  • Exact Mass: 321.15800
  • Monoisotopic Mass: 321.15762283g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 7
  • Complexity: 425
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.1
  • Topological Polar Surface Area: 76.1?2

Experimental Properties

  • Density: 1.225
  • PSA: 76.07000
  • LogP: 2.03800

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2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Cesium carbonate Solvents: Methanol ,  Water
1.2 Solvents: Dimethylformamide
Reference
Synthesis of kainoid analogs
Barraclough, Paul; Hudhomme, Pietrick; Spray, Caroline A.; Young, Douglas W., Tetrahedron, 1995, 51(14), 4195-212

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ;  overnight, rt
Reference
Design and synthesis of plant cyclopeptide Astin C analogs and investigation of their immunosuppressive activity
Li, Fei; Guo, Xi-Xi; Zeng, Guang-Zhi; Qin, Wei-Wei; Zhang, Bo; et al, Bioorganic & Medicinal Chemistry Letters, 2018, 28(14), 2523-2527

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Acetonitrile ,  Water
1.2 Reagents: Potassium carbonate Solvents: Dimethylformamide
Reference
Novel sulfur and selenium containing bis-α-amino acids from 4-hydroxyproline
Caputo, Romualdo; Della Greca, Marina; de Paola, Ivan; Mastroianni, Domenico; Longobardo, Luigi, Amino Acids, 2010, 38(1), 305-310

Production Method 4

Reaction Conditions
1.1 Reagents: Cesium carbonate Solvents: Methanol ,  Water ;  0 °C
1.2 Solvents: Dimethylformamide ;  12 h, 0 °C
Reference
Interstrand Dipole-Dipole Interactions Can Stabilize the Collagen Triple Helix
Shoulders, Matthew D.; Raines, Ronald T., Journal of Biological Chemistry, 2011, 286(26), 22905-22912

Production Method 5

Reaction Conditions
1.1 Reagents: Cesium carbonate Solvents: Methanol ,  Water ;  rt → 0 °C
1.2 Solvents: Dimethylformamide ;  0 °C; 20 h, rt
Reference
Discovery of subnanomolar arginine-glycine-aspartate-based αVβ3/αVβ5 integrin binders embedding 4-aminoproline residues
Zanardi, Franca; Burreddu, Paola; Rassu, Gloria; Auzzas, Luciana; Battistini, Lucia; et al, Journal of Medicinal Chemistry, 2008, 51(6), 1771-1782

2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate Raw materials

2-benzyl 1-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate Preparation Products

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