Boc-Glu-OBzl

Base Information

• Chemical Name: Boc-Glu-OBzl
• CAS No.: 30924-93-7
• Molecular Formula: C17H23NO6
• Molecular Weight: 337.373
• Hs Code.: 29242990
• European Community (EC) Number: 690-496-0
• DSSTox Substance ID: DTXSID20184917
• Nikkaji Number: J513.233I
• Mol file: 30924-93-7.mol

Synonyms:B-Glu-BE;t-Boc-glutamic acid alpha benzyl ester;tert-butyloxycarbonyl-glutamic acid 1-benzyl ester

Chemical Property of Boc-Glu-OBzl

Chemical Property:

• Vapor Pressure: 9.49E-12mmHg at 25°C
• Melting Point: 95.0 to 99.0 °C
• Refractive Index: -30 ° (C=0.7, MeOH)
• Boiling Point: 522.6 °C at 760 mmHg
• PKA: 4.48±0.10(Predicted)
• Flash Point: 269.859 °C
• PSA: 101.93000
• Density: 1.198 g/cm³
• LogP: 2.87880
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

99% ^*data from raw suppliers

Boc-glu-OBzl ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CCC(=O)O)C(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)O)C(=O)OCC1=CC=CC=C1
• Description: Boc-Glu-OBzl is an amino acid building block. It has been used in the synthesis of peptide-based inhibitors of human caspases and human rhinovirus (HRV) 3C protease that have enzyme inhibitory activity in vitro.
• Uses: Boc-L-Glutamic acid 1-benzyl ester is an effective substrate for vitamin K-dependent carboxylase,it is a monopeptide used to study the interaction of nucleic acid bases with peptides. N-Boc-L-glutamic Acid α-Benzyl Ester is an effective substrate for vitamin K-dependent carboxylase. N-Boc-L-glutamic Acid α-Benzyl Ester is a monopeptide used to study the interaction of nucleic acid bases with peptides.

Technology Process of Boc-Glu-OBzl

There total 8 articles about Boc-Glu-OBzl 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%

C31H33NO7 → Boc-Glu-OBn (30924-93-7)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; Irradiation;

DOI:10.1021/acscatal.7b02117

Reference yield: 98.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-benzyl L-glutamate (13030-09-6) → Boc-Glu-OBn (30924-93-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 0.5h;

DOI:10.1016/0223-5234(92)90117-J

Reference yield: 78.0%

Boc-Glu (2419-94-5) + benzyl alcohol (100-51-6,185532-71-2) → Boc-Glu-OBn (30924-93-7)

Guidance literature:

With ethylenediaminetetraacetic acid; rac-cysteine; papain; In dichloromethane; at 37 ℃; for 8h;

DOI:10.1016/S0040-4020(01)81493-9

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

1-benzyl L-glutamate

dicyclohexylamine salt of α-benzyl Boc-glutamate

di-tert-butyl dicarbonate

Downstream raw materials:

Boc-Glu(OSu)-OBn

(S)-2-tert-Butoxycarbonylamino-5-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-5-hydroxy-pentanoic acid benzyl ester

α-benzyl N^α-(tert-butyloxycarbonyl)-γ-<2-(trimethylsilyl)ethyl>-L-glutamate

(S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-(phenylselanyl)butanoate

Refernces

• 1、 Speckmeier, Elisabeth,Zeitler, Kirsten. "Desyl and phenacyl as versatile, photocatalytically cleavable protecting groups: A classic approach in a different (visible) light". . p. 6821 - 6826. Retrieved 2017/11/06.
• 2、 Gaunt, Matthew J.,Boschetti, Carlos E.,Yu, Jinquan,Spencer, Jonathan B.. "Preferential hydrogenolysis of NAP esters provides a new orthogonal protecting group strategy for carboxylic acids". . p. 1803 - 1806. Retrieved 2007/10/03.