2-({2-[2-(2-Aminoethoxy)ethoxy]ethoxy}methyl)-3-[(9H-fluoren-9-yl)methoxy]-3-oxopropanoic acid

Base Information

• Chemical Name: 2-({2-[2-(2-Aminoethoxy)ethoxy]ethoxy}methyl)-3-[(9H-fluoren-9-yl)methoxy]-3-oxopropanoic acid
• CAS No.: 867062-95-1
• Molecular Formula: C24H29 N O7
• Molecular Weight: 443.497
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID40693031
• Mol file: 867062-95-1.mol

Synonyms:SCHEMBL989369;DTXSID40693031;A841801;2-({2-[2-(2-Aminoethoxy)ethoxy]ethoxy}methyl)-3-[(9H-fluoren-9-yl)methoxy]-3-oxopropanoic acid;2-[2-[2-(2-azanylethoxy)ethoxy]ethoxymethyl]-3-(9H-fluoren-9-ylmethoxy)-3-oxidanylidene-propanoic acid

Chemical Property of 2-({2-[2-(2-Aminoethoxy)ethoxy]ethoxy}methyl)-3-[(9H-fluoren-9-yl)methoxy]-3-oxopropanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.571
• Boiling Point: 651.125 °C at 760 mmHg
• PKA: 4.28±0.10(Predicted)
• Flash Point: 347.588 °C
• PSA: 103.32000
• Density: 1.247g/cm³
• LogP: 3.44050
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly), Methanol (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 15
• Exact Mass: 443.19440226
• Heavy Atom Count: 32
• Complexity: 565

Purity/Quality:

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

Fmoc-12-amino-4,7,10-trioxadodecanoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)C(COCCOCCOCCN)C(=O)O
• Description: Fmoc-N-amido-PEG3-acid 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.
• Uses: 1-(9H-Fluoren-9-yl)-3-oxo-2,7,10,13-tetraoxa-4-azahexadecan-16-oic Acid has been used as a reactant for the preparation of vaccines.

Technology Process of 2-({2-[2-(2-Aminoethoxy)ethoxy]ethoxy}methyl)-3-[(9H-fluoren-9-yl)methoxy]-3-oxopropanoic acid

There total 8 articles about 2-({2-[2-(2-Aminoethoxy)ethoxy]ethoxy}methyl)-3-[(9H-fluoren-9-yl)methoxy]-3-oxopropanoic 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: 80.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoic acid hydrochloride salt → 12-{N-[(9H-fluoren-9-yl)methoxycarbonyl]amido}-4,7,10-trioxadodecanoic acid (867062-95-1,850312-72-0)

Guidance literature:

3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoic acid hydrochloride salt; With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 0.333333h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In tetrahydrofuran; water; at 0 - 20 ℃;

Reference yield: 69.0%

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-amido-4,7,10-trioxadodecanoic acid tert-butyl ester → 12-{N-[(9H-fluoren-9-yl)methoxycarbonyl]amido}-4,7,10-trioxadodecanoic acid (867062-95-1,850312-72-0)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 3h;

DOI:10.1039/c4ob01339e

Reference yield:

3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (186020-66-6,892154-71-1) → 12-{N-[(9H-fluoren-9-yl)methoxycarbonyl]amido}-4,7,10-trioxadodecanoic acid (867062-95-1,850312-72-0)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice

2: sodium azide / N,N-dimethyl-formamide / 17 h / 60 °C

3: sodium hydroxide; hydrogen / water; isopropyl alcohol / 15 h / 20 °C / pH 8 / Inert atmosphere

4: sodium hydrogencarbonate / water; acetone / 20 °C

5: trifluoroacetic acid / water / 3 h / 20 °C

With sodium azide; hydrogen; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; sodium hydroxide; In dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

DOI:10.1039/c4ob01339e

upstream raw materials:

3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

tert-Butyl 3-(2-(2-(2-azidoethoxyl)ethoxy)ethoxy)propanoate

tert-butyl 3-(2-{2-[2-(methanesulphonyloxy)ethoxy]ethoxy}ethoxy)propanoate

Refernces

• 1、 Tavernaro, Isabella,Hartmann, Sebastian,Sommer, Laura,Hausmann, Heike,Rohner, Christian,Ruehl, Martin,Hoffmann-Roeder, Anja,Schlecht, Sabine. "Synthesis of tumor-associated MUC1-glycopeptides and their multivalent presentation by functionalized gold colloids". . p. 81 - 97. Retrieved 2015/01/16.