ditert-butyl (2S)-2-aminopentanedioate

Base Information

• Chemical Name: ditert-butyl (2S)-2-aminopentanedioate
• CAS No.: 16874-06-9
• Molecular Formula: C13H25 N O4
• Molecular Weight: 259.346
• Hs Code.: 2922499990
• European Community (EC) Number: 240-900-2
• Nikkaji Number: J236.877C
• Wikidata: Q76085382
• Mol file: 16874-06-9.mol

Synonyms:di-tert-butyl glutamate;di-tert-butyl glutamate hydrochloride;glutamic acid di-tert-butyl ester;GTBE

Chemical Property of ditert-butyl (2S)-2-aminopentanedioate

Chemical Property:

• Vapor Pressure: 0.000574mmHg at 25°C
• Melting Point: 139-141 °C (dec.)
• Boiling Point: 311.1°Cat760mmHg
• PKA: 6.85±0.35(Predicted)
• Flash Point: 78.1°C
• PSA: 78.62000
• Density: 1.02g/cm³
• LogP: 2.47760
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 259.17835828
• Heavy Atom Count: 18
• Complexity: 299

Purity/Quality:

98%Min ^*data from raw suppliers

L-Glutamicacid,1,5-bis(1,1-dimethylethyl)ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of ditert-butyl (2S)-2-aminopentanedioate

There total 7 articles about ditert-butyl (2S)-2-aminopentanedioate 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: 94.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + isobutene (115-11-7,15220-85-6) → di-tert-butyl L-glutamate (16874-06-9)

Guidance literature:

With sulfuric acid; In dichloromethane; at -78 - 21 ℃; for 120h;

Reference yield: 29.0%

C39H55N3O11Se (1197815-07-8) → C18H31NO5Se (1197815-10-3) + di-tert-butyl L-glutamate (16874-06-9)

Guidance literature:

C₃₉H₅₅N₃O₁₁Se; With 1,4-dithiothreitol; In acetonitrile; for 5h; pH=7.6; aq. phosphate buffer; Inert atmosphere; UV-irradiation;

In acetonitrile; at 70 ℃; for 3h; pH=7.6; Inert atmosphere; aq. phosphate buffer;

DOI:10.1021/jo901368g

Reference yield: 26.0%

acetic acid tert-butyl ester (540-88-5) + L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → di-tert-butyl L-glutamate (16874-06-9)

Guidance literature:

With perchloric acid; at 0 - 20 ℃; for 48h;

DOI:10.1002/jlcr.3834

upstream raw materials:

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

L-glutamic acid

isobutene

N-benzyloxycarbonyl-L-glutamic acid

Downstream raw materials:

(S)-2-[2-(4-Nitro-phenyl)-acetylamino]-pentanedioic acid di-tert-butyl ester

di-tert-butyl (S)-N-(p-nitrobenzoyl)-glutamate

L-glutamic acid

L-glutamic acid 5-tert-butyl ester

Refernces

• 1、 Kang, Qi-Kai,Selvakumar, Sermadurai,Maruoka, Keiji. "Asymmetric Synthesis of α-Amino Acids by Organocatalytic Biomimetic Transamination". supporting information. p. 2294 - 2297. Retrieved 2019/04/10.
• 2、 -. "PRODRUGS ACTIVATED BY REACTIVE OXYGEN SPECIES FOR USE IN THE TREATMENT OF INFLAMMATORY DISEASES AND CANCER". Page/Page column 44; 45; 49. . Retrieved 2018/09/25.