Methyl (2S)-2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate

Base Information

• Chemical Name: Methyl (2S)-2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate
• CAS No.: 192314-71-9
• Molecular Formula: C16H27 N O7
• Molecular Weight: 345.393
• DSSTox Substance ID: DTXSID10450653
• Nikkaji Number: J964.476H
• Mol file: 192314-71-9.mol

Synonyms:192314-71-9;Methyl (2S)-2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate;Methyl(2S)-2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate;Methyl (S)-2-[Bis(Boc)amino]-5-oxopentanoate;(S)-METHYL 2-(BIS(TERT-BUTOXYCARBONYL)AMINO)-5-OXOPENTANOATE;L-Norvaline, N,N-bis[(1,1-dimethylethoxy)carbonyl]-5-oxo-, methyl ester;methyl (2S)-2-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-oxopentanoate;MFCD09839414;SCHEMBL16083949;DTXSID10450653;WEDVERRTEUYROC-NSHDSACASA-N;AS-78394;A4243;EN300-7465004;methyl (s)-2-di-t-butoxycarbonylamino-5-oxo-pentanoate;Methyl N,N-bis(tert-butoxycarbonyl)-5-oxo-L-norvalinate;(S)-Methyl 2-(bis(t-butoxycarbonyl)amino)-5-oxopentanoate;N,N-Bis(tert-butoxycarbonyl)-5-oxo-L-norvaline methyl ester;3-METHYL-5-PHENYL-1H-PYRAZOLE-4-CARBOXYLICACIDMETHYLESTER;methyl (2S)-2-{bis[(tert-butoxy)carbonyl]amino}-5-oxopentanoate

Chemical Property of Methyl (2S)-2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.466
• Boiling Point: 419.1°Cat760mmHg
• Flash Point: 207.2°C
• PSA: 99.21000
• Density: 1.12g/cm³
• LogP: 2.67930
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 345.17875220
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

97% ^*data from raw suppliers

(S)-Methyl2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl (2S)-2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate

There total 10 articles about Methyl (2S)-2-(bis(tert-butoxycarbonyl)amino)-5-oxopentanoate 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: 95.0%

(S)-dimethyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate (206128-03-2) → methyl (S)-2-N,N-di(tert-butoxycarbonyl)amino-5-oxopentanoate (192314-71-9)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; for 3h;

DOI:10.1055/s-0040-1706144

Reference yield: 62.0%

C18H32N2O8 (192314-70-8) → methyl (S)-2-N,N-di(tert-butoxycarbonyl)amino-5-oxopentanoate (192314-71-9)

Guidance literature:

With diisobutylaluminium hydride;

DOI:10.1002/anie.199711911

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl (S)-2-N,N-di(tert-butoxycarbonyl)amino-5-oxopentanoate (192314-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: DIBALH / tetrahydrofuran / -78 °C

With dmap; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-2003-40820

upstream raw materials:

C₁₈H₃₂N₂O₈

(S)-dimethyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate

L-glutamic acid dimethyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

methyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}-5-hydroxypentanoate

Boc-Lys-OH

C₄₆H₆₈N₄O₁₂

Refernces

• 1、 Sch?del, Nicole,Icik, Esra,Martini, Maike,Altevogt, Luca,Ramming, Isabell,Greulich, Andreas,Baro, Angelika,Bilitewski, Ursula,Laschat, Sabine. "Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine". supporting information. p. 2260 - 2268. Retrieved 2021/03/04.
• 2、 Krahn, Daniel,Heilmann, Geronimo,Vogel, Felix C. E.,Papadopoulos, Chrisovalantis,Zweerink, Susanne,Kaschani, Farnusch,Meyer, Hemmo,Roesch, Alexander,Kaiser, Markus. "Zelkovamycin is an OXPHOS Inhibitory Member of the Argyrin Natural Product Family". supporting information. p. 8524 - 8531. Retrieved 2020/07/02.