tert-Butyloxycarbonyl-L-isoglutamine benzyl ester

Base Information

• Chemical Name: tert-Butyloxycarbonyl-L-isoglutamine benzyl ester
• CAS No.: 18800-73-2
• Molecular Formula: C17H24N2O5
• Molecular Weight: 336.388
• UNII: XDU9X9WE1U
• ChEMBL ID: CHEMBL465932
• Mol file: 18800-73-2.mol

Synonyms:tert-Butyloxycarbonyl-L-isoglutamine benzyl ester;XDU9X9WE1U;UNII-XDU9X9WE1U;18800-73-2;benzyl (4S)-5-amino-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate;Pentanoic acid, 5-amino-4-(((1,1-dimethylethoxy)carbonyl)amino)-5-oxo-, phenylmethyl ester, (4S)-;BENZYL 5-AMINO-4-[(TERT-BUTOXYCARBONYL)AMINO]-5-OXOPENTANOATE;CHEMBL465932;SCHEMBL14997847;CCG-256524

Chemical Property of tert-Butyloxycarbonyl-L-isoglutamine benzyl ester

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 336.16852187
• Heavy Atom Count: 24
• Complexity: 439

Purity/Quality:

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)N
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)OCC1=CC=CC=C1)C(=O)N

Technology Process of tert-Butyloxycarbonyl-L-isoglutamine benzyl ester

There total 23 articles about tert-Butyloxycarbonyl-L-isoglutamine benzyl ester 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: 96.0%

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) + chloroformic acid ethyl ester (541-41-3) → benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate (18800-73-2,19238-66-5)

Guidance literature:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid; chloroformic acid ethyl ester; With triethylamine; In tetrahydrofuran; at -20 ℃; for 0.5h;

With ammonium hydroxide; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1002/chem.201706082

Reference yield: 96.0%

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate (18800-73-2,19238-66-5)

Guidance literature:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at -15 ℃; for 0.5h;

With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1002/chem.202004831

Reference yield: 89.0%

N-tert-butoxycarbonyl-D-glutamic acid α-p-nitrophenyl-γ-benzyl ester (76379-00-5) → benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate (18800-73-2,19238-66-5)

Guidance literature:

With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/ja0434376

upstream raw materials:

L-glutamic acid γ-benzyl ester

tert-butyl chloroformate

(S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-(2,5-dioxo-pyrrolidin-1-yl) ester

di-tert-butyl dicarbonate

Downstream raw materials:

D-α-glutamine

N-Fmoc-D-isoglutamine

N-tert-butyloxycarbonyl-O-benzyl glutamic nitrile

Refernces

• 1、 Cheng, Wei-Chieh,You, Ting-Yun,Teo, Zhen-Zhuo,Sayyad, Ashik A.,Maharana, Jitendra,Guo, Chih-Wei,Liang, Pi-Hui,Lin, Chung-Shun,Meng, Fan-Chun. "Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity". supporting information. p. 3836 - 3844. Retrieved 2020/10/21.
• 2、 Ngadjeua, Flora,Braud, Emmanuelle,Saidjalolov, Saidbakhrom,Iannazzo, Laura,Schnappinger, Dirk,Ehrt, Sabine,Hugonnet, Jean-Emmanuel,Mengin-Lecreulx, Dominique,Patin, Delphine,Ethève-Quelquejeu, Mélanie,Fonvielle, Matthieu,Arthur, Michel. "Critical Impact of Peptidoglycan Precursor Amidation on the Activity of l,d-Transpeptidases from Enterococcus faecium and Mycobacterium tuberculosis". supporting information. p. 5743 - 5747. Retrieved 2018/02/26.