tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate

Base Information

• Chemical Name: tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate
• CAS No.: 811442-84-9
• Molecular Formula: C15H32N2O6
• Molecular Weight: 336.429
• Hs Code.: 2924199090
• European Community (EC) Number: 877-018-8
• DSSTox Substance ID: DTXSID80470666
• Wikidata: Q72442412
• Mol file: 811442-84-9.mol

Synonyms:811442-84-9;tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate;t-Boc-N-amido-PEG4-Amine;Boc-NH-PEG4-CH2CH2NH2;BocNH-PEG4-CH2CH2NH2;16-AMINO-5,8,11,14-TETRAOXA-2-AZAHEXADECANOIC ACID 1,1-DIMETHYLETHYL ESTER;Tert-butyl N-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate;MFCD16619339;O-(2-Aminoethyl)-O'-[2-(Boc-amino)ethyl]triethylene Glycol;N1-Boc-3,6,9,12-tetraoxatetradecane-1,14-diamine;5,8,11,14-Tetraoxa-2-azahexadecanoic acid, 16-amino-, 1,1-dimethylethyl ester;WCNWLERBLMBSOT-UHFFFAOYSA-N;C15H32N2O6;1190008-84-4;Boc-NH-PEG4-amine;N-Methyl Pantoprazole-d3;Boc-N-amido-PEG4-Amine;Boc-amino-PEG-amine(n=4);SCHEMBL13788602;DTXSID80470666;tert-Butyl(14-amino-3,6,9,12-tetraoxatetradecyl)carbamate;BCP10868;EX-A3869;AKOS016009209;CS-W008352;DS-4475;HY-W008352;SB83292;s10757;BP-22602;SY113202;B6256;FT-0661800;EN300-1704347;A864600;O-(2-Aminoethyl)-O'-[2-(Boc-amino)ethyl]triethyleneglycol;tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecan-1-yl)carbamate;tert-butyl N-(14-amino-3,6,9,12-tetraoxatetradecan-1-yl)carbamate;2-(2-{2-[2-(2-Boc-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethylamine;5,8,11,14-Tetraoxa-2-azahexadecanoic acid,16-amino-,1,1-dimethyl ester;O-(2-Aminoethyl)-O inverted exclamation mark -[2-(Boc-amino)ethyl]triethylene Glycol

Chemical Property of tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate

Chemical Property:

• Boiling Point: 443.9±40.0 °C(Predicted)
• PKA: 12.23±0.46(Predicted)
• PSA: 101.27000
• Density: 1.059
• LogP: 1.62740
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 16
• Exact Mass: 336.22603674
• Heavy Atom Count: 23
• Complexity: 284

Purity/Quality:

98%,99%, ^*data from raw suppliers

O-(2-Aminoethyl)-O’-[2-(Boc-amino)ethyl]triethyleneGlycol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCOCCOCCOCCOCCN
• Description: t-Boc-N-amido-PEG4-amine is a Boc proteced PEG linker containing an free amino group. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The Boc group can be deprotected under mild acidic conditions to form the free amine.
• Uses: As a polyethyleneglycol (PEG) derivative, O-(2-AMinoethyl)-O'-[2-(Boc-aMino)ethyl]triethylene Glycol can be used in the preparation of fluorescent sensors for probing cyclodextrin and proteins.

Technology Process of tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)carbamate

There total 5 articles about tert-Butyl (14-amino-3,6,9,12-tetraoxatetradecyl)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: 92.0%

tert-butyl [2-(2-{2-[2-(2-azidoethoxy)ethoxy]ethoxy}ethoxy)ethyl]carbamate (940951-99-5) → tert-butyl N-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate (811442-84-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 10h; Solvent;

Reference yield: 64.0%

di-tert-butyl dicarbonate (24424-99-5) + 1,14-diamino-3,6,9,12-tetraoxatetradecane (68960-97-4,892154-56-2) → tert-butyl N-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate (811442-84-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ja4046907

Reference yield:

triethylene glycol monobenzyl tosyl ether (84131-04-4) → tert-butyl N-[2-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate (811442-84-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl acetamide / 10 h / 0 - 5 °C / Inert atmosphere

2: hydrogen; palladium on activated charcoal; hydrogenchloride / ethanol; water / 10 h / 50 °C

3: triethylamine; dmap / dichloromethane / 9 h / Cooling with ice

4: sodium azide / N,N-dimethyl-formamide / 8 h / 75 °C / Inert atmosphere

5: hydrogen; palladium 10% on activated carbon / ethanol / 10 h / 20 °C

With hydrogenchloride; dmap; sodium azide; palladium 10% on activated carbon; palladium on activated charcoal; hydrogen; sodium hydride; triethylamine; In ethanol; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

upstream raw materials:

di-tert-butyl dicarbonate

1,14-diamino-3,6,9,12-tetraoxatetradecane

triethylene glycol monobenzyl tosyl ether

tert-butyl N-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate

Downstream raw materials:

C₂₄H₄₀N₂O₈

C₃₉H₄₇F₁₂N₃O₁₁

C₃₄H₃₉F₁₂N₃O₉

C₄₁H₄₄F₁₂N₄O₁₂S

Refernces

• 1、 Ishida, Manabu,Watanabe, Hideaki,Takigawa, Kazumasa,Kurishita, Yasutaka,Oki, Choji,Nakamura, Akinobu,Hamachi, Itaru,Tsukiji, Shinya. "Synthetic self-localizing ligands that control the spatial location of proteins in living cells". supporting information. p. 12684 - 12689. Retrieved 2013/09/23.