Peg6-(CH2CO2H)2

Base Information

• Chemical Name: Peg6-(CH2CO2H)2
• CAS No.: 77855-76-6
• Molecular Formula: C₁₄H₂₆O₁₀
• Molecular Weight: 354.354
• DSSTox Substance ID: DTXSID001275957
• Nikkaji Number: J2.207.809G
• Mol file: 77855-76-6.mol

Synonyms:PEG6-(CH2CO2H)2;77855-76-6;3,6,9,12,15,18-Hexaoxaicosanedioic acid;3,6,9,12,15,18-Hexaoxaeicosanedioic acid;2-[2-[2-[2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic Acid;PEG6-Bis(acetic acid);HOOCCH2O-PEG5-CH2COOH;SCHEMBL20534906;DTXSID001275957;AKOS037653401;BP-23337;HY-122702;CS-0088436;C70490;3,6,9,12,15,18-Hexaoxaicosane-1,20-dioic acid

Chemical Property of Peg6-(CH2CO2H)2

Chemical Property:

• Boiling Point: 524.8±45.0 °C(Predicted)
• PKA: 3.09±0.10(Predicted)
• Density: 1.234±0.06 g/cm3(Predicted)
• Solubility.: Soluble in Water
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 19
• Exact Mass: 354.15259702
• Heavy Atom Count: 24
• Complexity: 280

Purity/Quality:

99.3% ^*data from raw suppliers

PEG6-(CH2CO2H)2 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(COCCOCCOCC(=O)O)OCCOCCOCC(=O)O
• Description: PEG6-(CH2CO2H)2 is a PEG linker containing two terminal carboxylic acid groups. The hydrophilic PEG spacer increases solubility in aqueous media. The terminal carboxylic acids can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Technology Process of Peg6-(CH2CO2H)2

There total 2 articles about Peg6-(CH2CO2H)2 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%

di-tert-butyl 3,6,9,12,15,18-hexaoxaicosane-1,20-dioate (211746-79-1) → 2-[2-[2-[2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid (77855-76-6,39927-08-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1021/jo980350s

Reference yield:

Pentaethylene glycol (4792-15-8) → 2-[2-[2-[2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid (77855-76-6,39927-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / aq. NaOH, Bu₄NHSO₄ / toluene / 1.) 0 deg C, 10 min, 2.) room temp., 30 min

2: 100 percent / CF₃COOH / CH₂Cl₂ / 1.5 h / Ambient temperature

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1021/jo980350s

Reference yield: 55.0%

(2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide (1448297-52-6) + 2-[2-[2-[2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid (77855-76-6,39927-08-7) → N1,N20-bis((S)-1-((2S,4R)-4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)-3,6,9,12,15,18-hexaoxaicosanediamide

Guidance literature:

(2S,4R)-1-[(2S)-2-azanyl-3,3-dimethylbutanoyl]-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]-4-oxidanylpyrrolidine-2-carboxamide; With benzotriazol-1-ol; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 220 ℃; for 0.0833333h;

2-[2-[2-[2-[2-[2-(carboxymethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetic acid; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; Time;

upstream raw materials:

di-tert-butyl 3,6,9,12,15,18-hexaoxaicosane-1,20-dioate

Pentaethylene glycol

Refernces

• 1、 Maniaci, Chiara,Hughes, Scott J.,Testa, Andrea,Chen, Wenzhang,Lamont, Douglas J.,Rocha, Sonia,Alessi, Dario R.,Romeo, Roberto,Ciulli, Alessio. "Homo-PROTACs: Bivalent small-molecule dimerizers of the VHL E3 ubiquitin ligase to induce self-degradation". . . Retrieved 2017/10/16.
• 2、 Wittmann, Valentin,Takayama, Shuichi,Gong, Ke Wei,Weitz-Schmidt, Gabriele,Wong, Chi-Huey. "Ligand Recognition by E- and P-Selectin: Chemoenzymatic Synthesis and Inhibitory Activity of Bivalent Sialyl Lewis x Derivatives and Sialyl Lewis x Carboxylic Acids". . p. 5137 - 5143. Retrieved 2007/10/03.