Boc-L-isoleucine

Base Information

• Chemical Name: Boc-L-isoleucine
• CAS No.: 13139-16-7
• Molecular Formula: C11H21NO4
• Molecular Weight: 231.292
• Hs Code.: 29241990
• European Community (EC) Number: 236-074-8
• DSSTox Substance ID: DTXSID40884508
• Nikkaji Number: J208.112A
• Wikidata: Q76145941
• ChEMBL ID: CHEMBL1229089
• Mol file: 13139-16-7.mol

Synonyms:Boc-L-isoleucine;13139-16-7;Boc-Ile-OH;Boc-DL-Ile-OH;116194-21-9;Boc-L-Ile-OH;N-(tert-Butoxycarbonyl)-L-isoleucine;N-Boc-L-isoleucine;tert-Butoxycarbonylisoleucine;Boc-DL-isoleucine;L-Isoleucine, N-[(1,1-dimethylethoxy)carbonyl]-;(2S,3S)-2-((tert-Butoxycarbonyl)amino)-3-methylpentanoic acid;(TERT-BUTOXYCARBONYL)-L-ISOLEUCINE;(2S,3S)-2-{[(Tert-Butoxy)Carbonyl]Amino}-3-Methylpentanoic Acid;(2S,3S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;tert-Butoxycarbonyl-L-isoleucine;tert-Butyloxycarbonyl-L-isoleucine;(2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoic acid;N-tert-Butoxycarbonyl-L-isoleucine;MFCD00038324;L-Isoleucine, N-((1,1-dimethylethoxy)carbonyl)-;tert-Butyloxycarbonylisoleucine;EINECS 236-074-8;N-(tert-Butyloxycarbonyl)-L-isoleucine;NSC 334311;Boc-Ile;N-Boc-Ile;Boc-(L)-isoleucine;BOC-ISOLEUCINE;N-((1,1-Dimethylethoxy)carbonyl)-L-isoleucine;Isoleucine, N-carboxy-, N-tert-butyl ester, L-;t-butoxycarbonylisoleucine;Boc-Ile-OH, 98%;BOC--L--Ile--OH;Boc-L-Isoleucine, 97%;t-butyloxycarbonylisoleucine;N-t-butoxycarbonylisoleucine;N-T-BOC-L-ISOLEUCINE;Boc-DL-Ile-OH, AldrichCPR;SCHEMBL627379;t-butyloxycarbonyl-L-isoleucine;CHEMBL1229089;DTXSID40884508;N-t-butyloxycarbonyl-L-isoleucine;HY-Z0438;N-(t-butyloxycarbonyl)-L-isoleucine;rel-(tert-Butoxycarbonyl)-isoleucine;MFCD00237550;AKOS010367326;AKOS015841932;CS-W020054;AS-12731;BP-12968;AM20080225;B1186;EN300-52855;N-.alpha.-(tert-Butoxycarbonyl)-L-Isoleucine;Isoleucine, N-[(1,1-dimethylethoxy)carbonyl]-;J-003398;N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-isoleucine;Z756427750;(2S,3S)-2-tert-butoxycarbonylamino-3-methyl-pentanoic acid;(2S,3S)-2-(tert-butoxycarbonyl-amino)-3-methyl-valeric acid

Chemical Property of Boc-L-isoleucine

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 68-72 °C
• Refractive Index: 2.7 ° (C=2, AcOH)
• Boiling Point: 356 °C at 760 mmHg
• PKA: 4.03±0.22(Predicted)
• Flash Point: 169.1 °C
• PSA: 75.63000
• Density: 1.061 g/cm³
• LogP: 2.40130
• Storage Temp.: −20°C
• Solubility.: Acetic Acid, DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 231.14705815
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: N-Boc-L-isoleucine is used to prepare BOC-L-isoleucine hydroxysuccinimide ester by using 1-hydroxybenzotriazole and 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride.

Technology Process of Boc-L-isoleucine

There total 54 articles about Boc-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: 100.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.07.084

Reference yield: 100.0%

→ N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7)

Guidance literature:

With trimethyltin(IV) hydroxide; In 1,2-dichloro-ethane; for 9h; Heating;

DOI:10.1016/S0040-4020(98)00805-9

Reference yield: 95.0%

N-(tert-butyloxycarbonyl) azide (1070-19-5) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) → N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7)

Guidance literature:

In 1,4-dioxane; sodium hydroxide; water; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2007.07.075

upstream raw materials:

isoleucine

di-tert-butyl dicarbonate

L-isoleucine

tert-Butyl 4-nitrophenyl carbonate

Downstream raw materials:

N-tert-butoxycarbonyl-L-isoleucine hydrazide

{(S)-1-[(S)-1-((1S,2S)-1-Hydrazinocarbonyl-2-methyl-butylcarbamoyl)-2-phenyl-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

Boc-Ile-Leu-OBzl

iBuOCO-Leu-OBzl

Refernces

• 1、 Anderson, James C.,Siddons, D. Craig,Smith, Stephen C.,Swarbrick, Martin E.. "Aza--Wittig Sigmatropic Rearrangement of Crotyl Amines". . p. 1835 - 1836. Retrieved 1995.
• 2、 Yuan, Feipeng,Hou, Zhen-Lin,Pramanick, Pranab K.,Yao, Bo. "Site-Selective Modification of α-Amino Acids and Oligopeptides via Native Amine-Directed γ-C(sp3)-H Arylation". . p. 9381 - 9385. Retrieved 2019.
• 3、 de Castro, Pedro P.,Siqueira, Raoni P.,Conforte, Luiza,Franco, Chris H.J.,Bressan, Gustavo C.,Amarante, Giovanni W.. "Cytotoxic activity of synthetic chiral amino acid derivatives". . p. 193 - 200. Retrieved 2019/12/28.
• 4、 Koplūnait?, Martyna,Butkut?, Kamil?,Me?kys, Rolandas,Taurait?, Daiva. "Synthesis of pyrimidine nucleoside and amino acid conjugates". supporting information. . Retrieved 2020/11/13.