Tert-butyl N-[5-(tosyloxy)pentyl]carbamate

Base Information

• Chemical Name: Tert-butyl N-[5-(tosyloxy)pentyl]carbamate
• CAS No.: 118811-34-0
• Molecular Formula: C17H27 N O5 S
• Molecular Weight: 357.471
• DSSTox Substance ID: DTXSID40445552
• Wikidata: Q82264007
• Mol file: 118811-34-0.mol

Synonyms:118811-34-0;5-(t-Boc-amino)-1-pentyl-p-toluenesulfonate;TERT-BUTYL N-[5-(TOSYLOXY)PENTYL]CARBAMATE;5-((TERT-BUTOXYCARBONYL)AMINO)PENTYL 4-METHYLBENZENESULFONATE;Carbamic acid,[5-[[(4-methylphenyl)sulfonyl]oxy]pentyl]-, 1,1-dimethylethyl ester (9CI);5-[(2-methylpropan-2-yl)oxycarbonylamino]pentyl 4-methylbenzenesulfonate;5-(tert-butoxycarbonylamino)pentyl 4-methylbenzenesulfonate;LCZC1193;SCHEMBL4640090;DTXSID40445552;RAOOQXZPVIXTHJ-UHFFFAOYSA-N;MFCD07776967;AKOS015914623;AS-81035;BP-28391;FT-0663460;J-003891;5-[(tert-Butoxycarbonyl)amino]pentyl 4-methylbenzene-1-sulfonate;1,1-Dimethylethyl N-[5-[[(4-methylphenyl)sulfonyl]oxy]pentyl]carbamate;Carbamic acid,[5-[[(4-methylphenyl)sulfonyl]oxy]pentyl]-,1,1-dimethylethyl ester(9ci)

Chemical Property of Tert-butyl N-[5-(tosyloxy)pentyl]carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 47-49°C
• Boiling Point: 501.854°C at 760 mmHg
• Flash Point: 257.312°C
• PSA: 90.08000
• Density: 1.136g/cm³
• LogP: 4.86700
• Storage Temp.: Refrigerator
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 357.16099414
• Heavy Atom Count: 24
• Complexity: 470

Purity/Quality:

98%min ^*data from raw suppliers

5-(t-Boc-amino)-1-pentyl-p-toluenesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCCCCCNC(=O)OC(C)(C)C
• Description: 5-((tert-Butoxycarbonyl)amino)pentyl 4-methylbenzenesulfonate is a PEG linker containing a Boc protected amine and a tosyl group. The protected amine can be deprotected under mild acidic conditions. The tosyl group is a very good leaving group for nucleophilic substitution reactions. The hydrophilic PEG spacer increases solubility in aqueous media.

Technology Process of Tert-butyl N-[5-(tosyloxy)pentyl]carbamate

There total 5 articles about Tert-butyl N-[5-(tosyloxy)pentyl]carbamate 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: 91.0%

N-(tert-butyloxycarbonyl)-5-aminopentanol (75178-90-4) + p-toluenesulfonyl chloride (98-59-9) → 5-((tert-butoxycarbonyl)amino)pentyl 4-methylbenzenesulfulfonate (118811-34-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 4.5h;

DOI:10.1016/j.bmcl.2013.01.092

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 5-((tert-butoxycarbonyl)amino)pentyl 4-methylbenzenesulfulfonate (118811-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane

2: triethylamine / dichloromethane

With triethylamine; In dichloromethane;

DOI:10.1002/chem.201202415

Reference yield:

5-hydroxypentylamine (2508-29-4) → 5-((tert-butoxycarbonyl)amino)pentyl 4-methylbenzenesulfulfonate (118811-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / dichloromethane

2: triethylamine / dichloromethane

With triethylamine; In dichloromethane;

DOI:10.1002/chem.201202415

upstream raw materials:

N-(tert-butyloxycarbonyl)-5-aminopentanol

p-toluenesulfonyl chloride

5-hydroxypentylamine

di-tert-butyl dicarbonate

Downstream raw materials:

(9H-fluoren-9-yl)methyl (5-(5-tosyl-1H-tetrazol-1-yl)pentyl)carbamate

[¹⁸F]-3-(4,5-dihydrooxazol-2-yl)phenyl (5-fluoropentyl)carbamate

C₂₅H₃₀N₅O₃⁽¹⁺⁾*Cl^(1-)

Cl^(1-)*C₂₅H₃₁N₄O₂⁽¹⁺⁾

Refernces

• 1、 Lamanna, Giuseppe,Smulski, Cristian R.,Chekkat, Neila,Estieu-Gionnet, Karine,Guichard, Gilles,Fournel, Sylvie,Bianco, Alberto. "Multimerization of an apoptogenic TRAIL-mimicking peptide by using adamantane-based dendrons". . p. 1762 - 1768. Retrieved 2013.
• 2、 Gotsbacher, Michael P.,Codd, Rachel. "Azido-Desferrioxamine Siderophores as Functional Click-Chemistry Probes Generated in Culture upon Adding a Diazo-Transfer Reagent". . p. 1433 - 1445. Retrieved 2020.
• 3、 -. "(4-HYDROXYPYRROLIDIN-2-YL)-HYDROXAMATE COMPOUNDS AND METHODS OF USE THEREOF". Paragraph 0710. . Retrieved 2019/05/15.