(S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid

Base Information

• Chemical Name: (S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid
• CAS No.: 73401-65-7
• Molecular Formula: C17H32 N2 O5
• Molecular Weight: 344.451
• DSSTox Substance ID: DTXSID40427191
• Nikkaji Number: J1.877.181K
• Wikidata: Q82239897
• Mol file: 73401-65-7.mol

Synonyms:Boc-leu-leu-OH;73401-65-7;(S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid;(2S)-4-methyl-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]pentanoic acid;N-[(1,1-Dimethylethoxy)carbonyl]-L-leucyl-L-leucine;Leucine, N-(N-carboxy-L-leucyl)-, N-tert-butyl methyl ester, L-;SCHEMBL7392267;L-Leucine, N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl-;DTXSID40427191;PBTNVAYSJPRTLQ-STQMWFEESA-N;MFCD00237559;AKOS015913893;AS-69495;HY-78008;CS-0007593;(2S)-2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanamido]-4-methylpentanoic acid;(S)-2-((S)-2-(tert-butoxycarbonylamino)-4-methylpentanamido)-4-methylpentanoic acid

Chemical Property of (S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid

Chemical Property:

• Boiling Point: 526.4±35.0 °C(Predicted)
• PKA: 3.50±0.10(Predicted)
• PSA: 111.71000
• Density: 1.064±0.06 g/cm3(Predicted)
• LogP: 3.58600
• Storage Temp.: -15°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 344.23112213
• Heavy Atom Count: 24
• Complexity: 441

Purity/Quality:

99%+, ^*data from raw suppliers

Boc-Leu-Leu-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid

There total 16 articles about (S)-2-((S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanamido)-4-methylpentanoic acid 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: 100.0%

Boc-Leu-Leu-OBzl (32925-57-8) → (S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoic acid (73401-65-7)

Guidance literature:

With 1% Pd/C; hydrogen; In ethyl acetate; at 20 ℃; for 2.5h; under 3750.38 Torr;

DOI:10.1021/jo902249w

Reference yield: 99.0%

N-tert-butoxycarbonyl-L-leucyl-L-leucine methyl ester (15136-13-7,88621-07-2,127636-68-4,132769-33-6,15136-12-6) → (S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoic acid (73401-65-7)

Guidance literature:

With sodium hydroxide; In methanol; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80998-4

Reference yield: 93.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + methyl (L)-leucinate hydrochloride (7517-19-3) → (S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoic acid (73401-65-7)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline;

DOI:10.1002/mrc.1270130111

upstream raw materials:

N-(N-tert-butoxycarbonyl-L-leucyl)-L-leucine ethyl ester

N-tert-butoxycarbonyl-L-leucine

methyl (L)-leucinate hydrochloride

N-tert-butoxycarbonyl-L-leucyl-L-leucine methyl ester

Downstream raw materials:

L-leucyl-L-leucine

methyl N²-(tert-butoxycarbonyl)-L-leucyl-L-leucyl-N⁶-(benzyloxycarbonyl)-L-lysinate

4-acetamidophenyl-N²-(tert-butoxycarbonyl)-L-leucyl-L-leucyl-N⁶-(benzylxycarbonyl)-L-lysinate

C₄₉H₇₅N₇O₁₁

Refernces

• 1、 Gulder, Tobias A. M.,Hong, Hanna,Correa, Jhonny,Egereva, Ekaterina,Wiese, Jutta,Imhoff, Johannes F.,Gross, Harald. "Isolation, structure elucidation and total synthesis of lajollamide a from the marine fungus Asteromyces cruciatus". . p. 2912 - 2935. Retrieved 2013/02/23.
• 2、 Hartwig, Sebastian,Schwarz, Jutta,Hecht, Stefan. "From peptides to their alternating ester-urea analogues: Synthesis and influence of hydrogen bonding motif and stereochemistry on aggregation". supporting information; experimental part. p. 772 - 782. Retrieved 2010/07/05.