Z-D-GLU-OH

Base Information

• Chemical Name: Z-D-GLU-OH
• CAS No.: 63648-73-7
• Molecular Formula: C13H15 N O6
• Molecular Weight: 281.265
• Hs Code.: 29225090
• European Community (EC) Number: 829-666-8
• Nikkaji Number: J25.181J
• Mol file: 63648-73-7.mol

Synonyms:Benzyloxycarbonyl-D-Glutamicacid; N-(Benzyloxycarbonyl)-D-glutamic acid; N-Carbobenzoxy-D-glutamic acid;NSC 169149

Chemical Property of Z-D-GLU-OH

Chemical Property:

• Melting Point: 120oC
• Refractive Index: 7.5 ° (C=8, AcOH)
• Boiling Point: 529.1 ºC at 760 mmHg
• PKA: 3.81±0.10(Predicted)
• Flash Point: 273.8 ºC
• PSA: 112.93000
• Density: 1.36 g/cm³
• LogP: 1.62170
• Storage Temp.: Store at RT.
• Solubility.: almost transparency in Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 281.08993720
• Heavy Atom Count: 20
• Complexity: 351

Purity/Quality:

99% ^*data from raw suppliers

Z-D-glutamic acid 99+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CCC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@H](CCC(=O)O)C(=O)O
• Uses: N-Cbz-D-glutamic acid is an N-Cbz-protected form of D-Glutamic acid (G596965). D-Glutamic acid is an unnatural isomer of L-Glutamic acid (G596960), and is found in bacterial cell wall peptidoglycan of gram-positive and gram-negative bacteria. D-Glutamic acid also occurs as poly-gamma-Glutamic acid, which is a weak immunogen but is capable of acting as a hapten (a small molecule that induces the production of antibodies, as well as binding to them).

Technology Process of Z-D-GLU-OH

There total 18 articles about Z-D-GLU-OH which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

N-(benzyloxy)carbonyl-D-glutamic acid 5-tert-butyl ester (51644-83-8) → N-benzyloxycarbonyl-D-glutamic acid (63648-73-7)

Guidance literature:

With phosphoric acid; In toluene; at 20 ℃; for 6h;

DOI:10.1021/jo061377b

Reference yield: 96.0%

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-D-glutamic acid (63648-73-7)

Guidance literature:

With sodium hydroxide; at 60 ℃; for 0.25h;

DOI:10.1021/jm0493313

Reference yield: 72.0%

Glutamic acid (617-65-2,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-DL-glutamic acid (1155-62-0,5619-01-2,63648-73-7)

Guidance literature:

DOI:10.1246/bcsj.62.2748

upstream raw materials:

Glutamic acid

benzyl chloroformate

benzyl-8-quinolyl carbonate

2-Benzyloxycarbonylamino-pentanedioic acid dimethyl ester

Downstream raw materials:

D-Glutamic acid

L-glutamic acid

benzyloxycarbonylglutamic acid dimethyl ester

diphenacyl benzyloxycarbonylglutamate

Refernces

• 1、 Eey, Stanley T.-C.,Lear, Martin J.. "Total synthesis of (-)-platensimycin by advancing oxocarbenium- and iminium-mediated catalytic methods". . p. 11556 - 11573. Retrieved 2015/01/16.
• 2、 Lawandi, Janice,Toumieux, Sylvestre,Seyer, Valentine,Campbell, Philip,Thielges, Sabine,Juillerat-Jeanneret, Lucienne,Moitessier, Nicolas. "Constrained peptidomimetics reveal detailed geometric requirements of covalent prolyl oligopeptidase inhibitors". experimental part. p. 6672 - 6684. Retrieved 2010/04/28.