Boc-L-glutamic acid dibenzyl ester

Base Information

• Chemical Name: Boc-L-glutamic acid dibenzyl ester
• CAS No.: 80963-14-0
• Molecular Formula: C24H29NO6
• Molecular Weight: 427.497
• DSSTox Substance ID: DTXSID90560087
• Nikkaji Number: J514.103F
• Wikidata: Q82443070
• Mol file: 80963-14-0.mol

Synonyms:BOC-L-GLUTAMIC ACID DIBENZYL ESTER;80963-14-0;dibenzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate;SCHEMBL1517760;DTXSID90560087;NRRBBBBGBKFGII-FQEVSTJZSA-N;Dibenzyl N-(tert-butoxycarbonyl)-L-glutamate;N-tert-Butyloxycarbonyl-L-glutamic acid dibenzyl ester

Chemical Property of Boc-L-glutamic acid dibenzyl ester

Chemical Property:

• PSA: 90.93000
• LogP: 4.53760
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 427.19948764
• Heavy Atom Count: 31
• Complexity: 573

Purity/Quality:

97% ^*data from raw suppliers

BOC-L-GLUTAMIC ACID DIBENZYL ESTER 95.00% ^*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)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CCC(=O)OCC1=CC=CC=C1)C(=O)OCC2=CC=CC=C2

Technology Process of Boc-L-glutamic acid dibenzyl ester

There total 5 articles about Boc-L-glutamic acid dibenzyl 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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + L-glutamic acid dibenzyl ester 4-toluenesulfonate (2791-84-6,227205-81-4) → dibenzyl N-tert-butyloxycarbonyl-L-glutamate (80963-14-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 19h;

DOI:10.1016/j.bmc.2004.10.006

Reference yield: 46.0%

Boc-Glu (2419-94-5) + benzyl bromide (100-39-0) → dibenzyl N-tert-butyloxycarbonyl-L-glutamate (80963-14-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → dibenzyl N-tert-butyloxycarbonyl-L-glutamate (80963-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tBuN=P(NMe₂)3 / acetonitrile / 16 h / 20 °C

2: acetonitrile / 6 h / 20 °C

With tert-butylimino-tris(dimethylamino)phosphorane; In acetonitrile;

DOI:10.1021/ol020136x

upstream raw materials:

Boc-Glu

benzyl bromide

di-tert-butyl dicarbonate

L-glutamic acid dibenzyl ester 4-toluenesulfonate

Downstream raw materials:

L-glutamic acid dibenzyl ester hydrochloride

dibenzyl L-glutamate

dibenzyl (γS)-N-tert-butyloxycarbonyl-L-γ-allylglutamate

Boc-Glu(Bzl)-NH-NH-Ph

Refernces

• 1、 -. "SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF". Page/Page column 77. . Retrieved 2018/03/09.
• 2、 Palomo, Claudio,Palomo, Antonio L,Palomo, Francisco,Mielgo, Antonia. "Soluble alpha-amino acid salts in acetonitrile: practical technology for the production of some dipeptides.". . p. 4005 - 4008. Retrieved 2007/10/03.