Boc-N-methyl-L-isoleucine

Base Information

• Chemical Name: Boc-N-methyl-L-isoleucine
• CAS No.: 52498-32-5
• Molecular Formula: C₁₂H₂₃NO₄
• Molecular Weight: 245.319
• European Community (EC) Number: 805-207-7
• DSSTox Substance ID: DTXSID80426926
• Nikkaji Number: J1.903.284A
• Wikidata: Q72449957
• Mol file: 52498-32-5.mol

Synonyms:52498-32-5;Boc-N-methyl-L-isoleucine;(2S,3S)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylpentanoic acid;Boc-MeIle-OH;Boc-N-a-methyl-L-isoleucine;Boc-N-|A-Methyl-L-isoleucine;L-Isoleucine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-;(2S,3S)-3-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoic acid;n-(tert-butoxycarbonyl)-n-methyl-l-isoleucine;n-alpha-t-Butyloxycarbonyl-N-alpha-methy-L-isoleucine;N-alpha-t-Butyloxycarbonyl-N-alpha-methyl-L-isoleucine;Boc-L-MeIle-OH;BOC-N-methyl-isoleucine;SCHEMBL67051;DTXSID80426926;HTBIAUMDQYXOFG-IUCAKERBSA-N;MFCD00066105;AKOS015892886;AM81858;CS-W012716;HY-W012000;DS-16131;Boc-N-Me-Ile-OH, >=97.0% (HPLC);EN300-6732088;(2s,3s)-2-(t-butoxycarbonyl(methyl)amino)-3-methylpentanoic acid;(2S,3S)-2-((tert-Butoxycarbonyl)(methyl)amino)-3-methylpentanoicacid;(2S,3S)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylpentanoic acid;(2S,3S)-2-(tert-butoxycarbonyl-methyl-amino)-3-methyl-pentanoic acid;(2S,3S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-methylpentanoic acid

Chemical Property of Boc-N-methyl-L-isoleucine

Chemical Property:

• Vapor Pressure: 1.86E-05mmHg at 25°C
• Refractive Index: 1.466
• Boiling Point: 338.175 °C at 760 mmHg
• PKA: 4.05±0.22(Predicted)
• Flash Point: 158.323 °C
• PSA: 66.84000
• Density: 1.053 g/cm³
• LogP: 2.35260
• Storage Temp.: Store at RT.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 245.16270821
• Heavy Atom Count: 17
• Complexity: 283

Purity/Quality:

98% ^*data from raw suppliers

Boc-N-methyl-L-isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Boc-N-methyl-L-isoleucine

There total 10 articles about Boc-N-methyl-L-isoleucine 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: 98.0%

N-tert-butyloxy-isoleucine (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9) + methyl iodide (74-88-4) → (2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]-3-methylpentanoic acid (52498-32-5,53462-50-3,136092-80-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 26h; Inert atmosphere;

DOI:10.1007/s00044-016-1555-5

Reference yield: 92.0%

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) + methyl iodide (74-88-4) → (2S,3S)-2-[N-(tert-butoxycarbonyl)-N-methyl]amino-3-methylpentanoic acid (53462-50-3,136092-80-3,52498-32-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 25 ℃; for 36h;

DOI:10.17344/acsi.2016.2322

Reference yield: 92.0%

(S)-4-sec-Butyl-5-oxo-oxazolidine-3-carboxylic acid tert-butyl ester → (2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]-3-methylpentanoic acid (52498-32-5,53462-50-3,136092-80-3)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1246/cl.1999.299

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-isoleucine

methyl iodide

dimethyl sulfate

L-isoleucine

Downstream raw materials:

dolastatin 10

Refernces

• 1、 Wunder, Anja,Rothemund, Matthias,Schobert, Rainer. "Synthesis and anticancer activity of the proposed structure of caldoramide, an N-peptidyltetramate from the cyanobacterium Caldora penicillata". supporting information. p. 5138 - 5142. Retrieved 2018/04/16.
• 2、 Zhou, Wen,Nie, Xiao-Di,Zhang, Yu,Si, Chang-Mei,Zhou, Zhu,Sun, Xun,Wei, Bang-Guo. "A practical approach to asymmetric synthesis of dolastatin 10". . p. 6119 - 6131. Retrieved 2017/08/02.