5-[(2-Methylpropan-2-yl)oxy]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid

Base Information

• Chemical Name: 5-[(2-Methylpropan-2-yl)oxy]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid
• CAS No.: 5891-45-2
• Molecular Formula: C17H23NO6
• Molecular Weight: 337.373
• NSC Number: 169169
• DSSTox Substance ID: DTXSID40305122
• Mol file: 5891-45-2.mol

Synonyms:5-[(2-methylpropan-2-yl)oxy]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid;4-(((Benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid;2096546-37-9;MFCD00077016;Z-L-glutamic acid alpha-tert-butyl ester;NSC169169;starbld0039306;SCHEMBL5970914;DTXSID40305122;VJECGKAFPHEJQS-UHFFFAOYSA-N;AKOS015902089;NSC-169169;Z-L-glutamic acid |A-tert-butyl ester;SY061060;Z-L-glutamic acid alpha-tert.butyl ester;FT-0686535;2-Benzyloxycarbonylamino-pentanedioic acid l-tert-butyl ester;4-{[(Benzyloxy)carbonyl]amino}-5-tert-butoxy-5-oxopentanoic acid (non-preferred name)

Chemical Property of 5-[(2-Methylpropan-2-yl)oxy]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid

Chemical Property:

• Vapor Pressure: 9.49E-12mmHg at 25°C
• Melting Point: 81.0 to 85.0 °C
• Refractive Index: 1.523
• Boiling Point: 522.6 °C at 760 mmHg
• PKA: 4.48±0.10(Predicted)
• Flash Point: 269.9 °C
• PSA: 101.93000
• Density: 1.197 g/cm³
• LogP: 2.87880
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 337.15253745
• Heavy Atom Count: 24
• Complexity: 437

Purity/Quality:

95% ^*data from raw suppliers

1-tert-Butyl N-Carbobenzoxy-L-glutamate >98.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CCC(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: A protected glutamic acid for use in peptide synthesis.

Technology Process of 5-[(2-Methylpropan-2-yl)oxy]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid

There total 25 articles about 5-[(2-Methylpropan-2-yl)oxy]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoic acid 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: 100.0%

tert-butyl N-benzyloxycarbonyl-L-pyroglutamate (81470-51-1) → (S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1021/jm00107a013

Reference yield:

1-tert-butyl 5-methyl (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioate (57732-63-5) → (S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2)

Guidance literature:

(saponification);

DOI:10.1039/j39680001219

Reference yield:

Cbz-L-pGlu-OH (32159-21-0) → (S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester (5891-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70percent perchloric acid / Ambient temperature

2: 100 percent / 1 M KOH / methanol

With potassium hydroxide; perchloric acid; In methanol;

DOI:10.1021/jm00107a013

upstream raw materials:

acetic acid tert-butyl ester

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester

1-tert-butyl 5-methyl (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioate

di-tert-butyl N-Cbz-L-glutamate

Downstream raw materials:

N-(N-benzyloxycarbonyl-L-γ-glutamyl)-glycine

N-(N-Benzyloxycarbonyl-L-γ-glutamyl-1-tert.-butylester)-glycin-tert.-butylester

(S)-2-Benzyloxycarbonylamino-4-(2-hydroxy-hexylcarbamoyl)-butyric acid tert-butyl ester

(S)-2-Benzyloxycarbonylamino-4-(2-hydroxy-3-morpholin-4-yl-propylcarbamoyl)-butyric acid tert-butyl ester

Refernces

• 1、 Bhat, Ramakrishna G.,Porhiel, Emmanuel,Saravanan, Vadivelu,Chandrasekaran, Srinivasan. "Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues". . p. 5251 - 5253. Retrieved 2007/10/03.
• 2、 Sullins, David W.,Bobik, Thomas A.,Wolfe, Ralph S.,Rinehart, Kenneth L.. "Total synthesis of the methanogenic cofactors methanofuran and methanofuran b". . p. 6646 - 6651. Retrieved 2007/10/02.