2-{[(Benzyloxy)carbonyl]amino}-4-methylpentanoic acid

Base Information

• Chemical Name: 2-{[(Benzyloxy)carbonyl]amino}-4-methylpentanoic acid
• CAS No.: 3588-60-1
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.309
• Hs Code.: 29242990
• NSC Number: 523826,60039
• DSSTox Substance ID: DTXSID90289266
• Nikkaji Number: J2.792.820J
• Mol file: 3588-60-1.mol

Synonyms:3588-60-1;Z-DL-Leu-OH;N-Carbobenzoxy-DL-leucine;2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoic acid;cbz-dl-leucine;4-methyl-2-(phenylmethoxycarbonylamino)pentanoic acid;2-(benzyloxycarbonylamino)-4-methylpentanoic acid;Z-DL-leucine;cbz-leu-oh;Z-D-Leucin;Cbz-D-Leu-OH;N-(Benzyloxycarbonyl)-DL-leucine;2-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid;MFCD00026494;MFCD00066068;NSC-60039;N-alpha-Carbobenzoxy-DL-leucine;NSC 523826;N-Cbz-DL-leucine;dl-Leucine, N-[(phenylmethoxy)carbonyl]-;Leucine, N-carboxy-, N-benzyl ester, dl-;N-carbobenzyloxy-DL-leucine;((Benzyloxy)carbonyl)leucine;N-benzyloxycarbonyl-DL-leucine;SCHEMBL1823902;DTXSID90289266;N-(Benzyloxycarbonyl)-d,l-leucine;N-[(Benzyloxy)carbonyl]leucine #;NSC60039;MFCD00065129;NSC523826;Z-DL-Leu-OH, >=98.0%;AKOS000169735;AKOS025243658;AB01476;AB02682;FD21923;NSC-523826;AS-49243;SY062054;SY062056;CS-0112504;FT-0610892;FT-0629945;FT-0629956;EN300-84286;A874502;A904505;Z285919526

Chemical Property of 2-{[(Benzyloxy)carbonyl]amino}-4-methylpentanoic acid

Chemical Property:

• Appearance/Colour: White or colorless powder
• Melting Point: 54 °C
• Boiling Point: 442.8 °C at 760 mmHg
• PKA: 4.00±0.21(Predicted)
• Flash Point: 221.6 °C
• PSA: 75.63000
• Density: 1.158 g/cm³
• LogP: 2.80300
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Ethanol (Slight
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 298

Purity/Quality:

≥98% ^*data from raw suppliers

Z-DL-leucine ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Description: It is a biologically active amino acid usually used as nutritional supplements, flavour enhancer, and components for preparing pharmaceutical and biochemical products such as amino acid infusion and comprehensive amino acid, hypoglycemic agent, plant growth promoter. Specifically, it is found that ingestion of a high whey protein, leucine-enriched supplement resulted in a larger overall postprandial muscle protein synthesis rate in healthy older people compared with a conventional dairy product.1 Moreover, this substance possesses the most marked anabolic characteristics in acting as a trigger element for the initiation of protein synthesis, thus guaranteeing the healthy human skeleton muscle metabolism.2 In addition, this chemical may be involved in the promotion of plant growth.3

Technology Process of 2-{[(Benzyloxy)carbonyl]amino}-4-methylpentanoic acid

There total 11 articles about 2-{[(Benzyloxy)carbonyl]amino}-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%

benzyl chloroformate (501-53-1,94274-21-2) + LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1) → N-carbobenzyloxy leucine (2018-66-8,28862-79-5,3588-60-1)

Guidance literature:

With sodium hydroxide; In water; at 0 - 20 ℃;

DOI:10.1128/AAC.01152-16

Reference yield: 91.0%

methyl ((benzyloxy)carbonyl)leucinate → N-carbobenzyloxy leucine (2018-66-8,28862-79-5,3588-60-1)

Guidance literature:

With sodium hydroxide; water; for 16h; Ambient temperature;

DOI:10.1039/a707067e

Reference yield: 72.0%

3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester (91806-74-5) + LEUCINE (328-39-2,21675-61-6,25248-98-0,70-45-1) → N-carbobenzyloxy leucine (2018-66-8,28862-79-5,3588-60-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -5 ℃; for 5h;

DOI:10.1016/S0040-4020(98)00947-8

upstream raw materials:

benzyl-8-quinolyl carbonate

LEUCINE

3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

D(L)-Z-Leu-PNP

N-(N-benzyloxycarbonyl-DL-leucyl)-N'-isonicotinoyl-hydrazine

N-benzyloxycarbonyl-DL-leucine cyanomethyl ester

N-benzyloxycarbonyl-DL-thioleucine S-phenyl ester

Refernces

• 1、 Dola, Vasantha Rao,Soni, Awakash,Agarwal, Pooja,Ahmad, Hafsa,Raju, Kanumuri Siva Rama,Rashid, Mamunur,Wahajuddin, Muhammad,Srivastava, Kumkum,Haq,Dwivedi,Puri,Katti. "Synthesis and evaluation of chirally defined side chain variants of 7-chloro-4-aminoquinoline to overcome drug resistance in malaria chemotherapy". . . Retrieved 2017/03/09.
• 2、 Zheng, Yongpeng,Xu, Jiaxi. "Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids". . p. 5197 - 5206. Retrieved 2014/12/10.