FMoc-NH-8(ethylene glycol)-acetic acid

Base Information

• Chemical Name: FMoc-NH-8(ethylene glycol)-acetic acid
• CAS No.: 868594-52-9
• Molecular Formula: C₃₃H₄₇NO₁₂
• Molecular Weight: 649.736
• Hs Code.: 2942000090
• Mol file: 868594-52-9.mol

Synonyms:FMoc-NH-8(ethylene glycol)-acetic acid;FMoc-NH-PEG8-CH2COOH;5,8,11,14,17,20,23,26-Octaoxa-2-azaoctacosanedioic acid 1-(9H-fluoren-9-ylmethyl) ester;Fmoc-NH-PEG8-CH2CO2H

Chemical Property of FMoc-NH-8(ethylene glycol)-acetic acid

Chemical Property:

• Boiling Point: 773.7±60.0 °C(Predicted)
• PKA: 3.39±0.10(Predicted)
• PSA: 149.47000
• Density: 1.201±0.06 g/cm3(Predicted)
• LogP: 3.13340

Purity/Quality:

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

Fmoc-NH-8(ethyleneglycol)-acticacid min.97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Fmoc-NH-PEG8-CH2COOH is a PEG linker containing an Fmoc-protected amine and a terminal carboxylic acid. The hydrophilic PEG spacer increases solubility in aqueous media. The Fmoc group can be deprotected under basic condition to obtain the free amine which can be used for further conjugations. The terminal carboxylic acid 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 FMoc-NH-8(ethylene glycol)-acetic acid

There total 7 articles about FMoc-NH-8(ethylene glycol)-acetic acid 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: 99.0%

C37H55NO12 → 26-(fluoren-9-ylmethyloxycarbonylamino)-3,6,9,12,15,18,21,24-octaoxahexaeicosanoic acid (868594-52-9)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1039/c8cc09151j

Reference yield: 70.0%

26-(fluoren-9-ylmethyloxycarbonylamino)-3,6,9,12,15,18,21,24-octaoxahexaeicosan-1-ol (868594-51-8) → 26-(fluoren-9-ylmethyloxycarbonylamino)-3,6,9,12,15,18,21,24-octaoxahexaeicosanoic acid (868594-52-9)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetone; at 0 - 20 ℃;

DOI:10.1002/ejoc.200701188

Reference yield:

Tetraethylene glycol (112-60-7) → 26-(fluoren-9-ylmethyloxycarbonylamino)-3,6,9,12,15,18,21,24-octaoxahexaeicosanoic acid (868594-52-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thionyl chloride; triethylamine; dmap / dichloromethane / 0 °C

1.2: 20 °C

2.1: sodium hydride / tetrahydrofuran / 20 °C

2.2: 20 °C

3.1: sodium hydride / tetrahydrofuran / 0 °C

4.1: triphenylphosphine / tetrahydrofuran; water / 20 °C

4.2: 20 °C

5.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 20 °C

With dmap; thionyl chloride; sodium hydride; methoxybenzene; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1039/c8cc09151j

upstream raw materials:

26-(fluoren-9-ylmethyloxycarbonylamino)-3,6,9,12,15,18,21,24-octaoxahexaeicosan-1-ol

Tetraethylene glycol

2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethanol

α-(2-azidoethyl)-ω-hydroxyhexa(oxyethylene)

Refernces

• 1、 Pilkington-Miksa, Michael A.,Sarkar, Supti,Writer, Michele J.,Barker, Susie E.,Shamlou, Parviz Ayazi,Hart, Stephen L.,Hailes, Helen C.,Tabor, Alethea B.. "Synthesis of bifunctional integrin-binding peptides containing PEG spacers of defined length for non-viral gene delivery". experimental part. p. 2900 - 2914. Retrieved 2009/04/11.