5-O-benzyl 1-O-(4-nitrophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate

Base Information

• Chemical Name: 5-O-benzyl 1-O-(4-nitrophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
• CAS No.: 7536-59-6
• Molecular Formula: C23H26N2O8
• Molecular Weight: 458.468
• DSSTox Substance ID: DTXSID90394526
• Mol file: 7536-59-6.mol

Synonyms:7536-59-6;Boc-L-Glu(Bzl)-ONp;AC1MU65R;SCHEMBL12082260;DTXSID90394526;5-O-benzyl 1-O-(4-nitrophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate;FT-0655371;A838392;SR-01000507293;SR-01000507293-1;BOC-L-GLUTAMIC ACID GAMMA-BENZYL ESTER P-NITROPHENYL ESTER;N(T-BUTOXYCARBONYL)L-GLUTAMIC ACID GAMMA-BENZYL ESTER ALPHA(4NITROPHENYL) ESTER;O1-(4-nitrophenyl) O5-(phenylmethyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate;5-O-benzyl 1-O-(4-nitrophenyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate

Chemical Property of 5-O-benzyl 1-O-(4-nitrophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate

Chemical Property:

• Boiling Point: 618.0±55.0 °C(Predicted)
• PKA: 10.62±0.46(Predicted)
• PSA: 136.75000
• Density: 1.258±0.06 g/cm3(Predicted)
• LogP: 4.83120
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 458.16891579
• Heavy Atom Count: 33
• Complexity: 671

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-L-glutamic acid γ-benzyl ester alpha-4-nitrophenyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCC(=O)OCC1=CC=CC=C1)C(=O)OC2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of 5-O-benzyl 1-O-(4-nitrophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate

There total 6 articles about 5-O-benzyl 1-O-(4-nitrophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate 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: 51.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid (117997-81-6) → 4-nitrophenyl γ-benzyl-N-tert-butoxycarbonylglutamate (7536-59-6,76379-00-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; 1) 0 deg C, 1 h, 2) 20 deg C, overnight;

DOI:10.1135/cccc19951765

Reference yield: 48.0%

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Boc-Glu(OBzl)-OH (13574-13-5) → Boc-Glu(OBzl)-ONp (7536-59-6)

Guidance literature:

With dicyclohexyl-carbodiimide;

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + L-glutamic acid γ-benzyl ester (1676-73-9,25014-27-1) + tert-Butyl 4-nitrophenyl carbonate (13303-10-1) → Boc-Glu(OBzl)-ONp (7536-59-6)

Guidance literature:

Multistep reaction; (i) Et₃N, (ii) DCC, /BRN= 1281877/;

DOI:10.1002/hlca.19630460518

upstream raw materials:

4-nitro-phenol

5-(benzyloxy)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid

Boc-Glu(OBzl)-OH

L-glutamic acid γ-benzyl ester

Downstream raw materials:

γ-benzyl-glutamic acid amide

bis-(γ-benzyl-glutamic acid)hexamethylenediamide

benzyl Nα-Boc-(γ-benzyl α-L-glutamyl)-Nω-nitro-L-argininate

Nα-[N-Boc-(γ-benzyl) α-L-glutamyl]-N-[1-(diethoxyphosphoryl)-2,3-dihydro-1H-inden-1-yl]-Nω-nitro-L-argininamide

Refernces

• 1、 Masar, Bohumil,Schmidt, Pavel,Pivcova, Hana,Cefelin, Pavel. "α-AMINOACYL DERIVATIVES OF α,ω-DIAMINOPOLY(OXYETHYLENE)". . p. 1922 - 1927. Retrieved 2007/10/02.