ditert-butyl (2S)-2-aminobutanedioate

Base Information

• Chemical Name: ditert-butyl (2S)-2-aminobutanedioate
• CAS No.: 13795-73-8
• Molecular Formula: C12H23NO4
• Molecular Weight: 245.319
• DSSTox Substance ID: DTXSID00428487
• Nikkaji Number: J283.182A
• Wikidata: Q82241319
• Mol file: 13795-73-8.mol

Synonyms:H-Asp(OtBu)-OtBu;13795-73-8;ditert-butyl (2S)-2-aminobutanedioate;D-aspartic acid di-t-butyl ester;Aspartic acid di-tert-butyl ester;di-t-butyl aspartate;di-tert-butyl aspartate;di-tert-butyl L-aspartate;SCHEMBL975517;DTXSID00428487;FNCGNFXGKHSMKJ-QMMMGPOBSA-N;H-Asp (OtBu)-OtBu hydrochloride;(s)-di-tert-butyl 2-aminosuccinate;L-aspartic acid di-tert-butyl ester;AKOS030213034;CS-0497670

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

Chemical Property:

• PSA: 78.62000
• LogP: 2.08750
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 245.16270821
• Heavy Atom Count: 17
• Complexity: 286

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 11 articles about ditert-butyl (2S)-2-aminobutanedioate 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: 70.0%

1,4-di-tert-butyl (2S)-2-{[(benzyloxy)carbonyl]amino}butanedioate (42417-76-5) → L-aspartic acid di-tert-butyl ester (13795-73-8)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In methanol; at 20 ℃;

DOI:10.1021/jacs.6b01327

Reference yield: 39.0%

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + tert-butyl methyl ether (1634-04-4) → L-aspartic acid di-tert-butyl ester (13795-73-8)

Guidance literature:

With sulfuric acid; at 25 ℃; for 2h; chemoselective reaction; Molecular sieve;

DOI:10.1016/j.tetlet.2011.11.108

Reference yield:

N-(diphenylmethylene)glycine tert-butyl ester (81477-94-3) + t-butyl iodoacetate (49827-15-8) → L-aspartic acid di-tert-butyl ester (13795-73-8) + tert-butyl (R)-3-(carbo-tert-butoxy)-2-aminopropanoate

Guidance literature:

With potassium hydroxide; hydrogen cation; N-anthracenyl methyl cinchonidium chloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) PhMe, H₂O, 4 h, RT; 2.) H₂O;

DOI:10.1016/S0040-4039(97)10293-3

upstream raw materials:

acetic acid tert-butyl ester

L-Aspartic acid

N-Cbz-L-Asp

β-tert.-butyl>-L-asparagin-tert.-butylester

Downstream raw materials:

C₁₉H₂₆N₂O₈

Refernces

• 1、 Tsai, Fu-Te,Wang, Yanyan,Darensbourg, Donald J.. "Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum-Polymer Conjugates". supporting information. p. 4626 - 4633. Retrieved 2016/05/19.
• 2、 Rull, Jordi,Jara, José Juan,Sebastián, Rosa M.,Vallribera, Adelina,Nájera, Carmen,Majoral, Jean-Pierre,Caminade, Anne-Marie. "Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts". . p. 2049 - 2056. Retrieved 2016/07/07.