DBCO-PEG4-Acid

Base Information

• Chemical Name: DBCO-PEG4-Acid
• CAS No.: 1537170-85-6
• Molecular Formula: C₃₀H₃₆N₂O₈
• Molecular Weight: 552.624
• Mol file: 1537170-85-6.mol

Synonyms:

Chemical Property of DBCO-PEG4-Acid

Chemical Property:

• Boiling Point: 839.7±65.0 °C(Predicted)
• PKA: 4.28±0.10(Predicted)
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO, DCM, DMF

Purity/Quality:

97% ^*data from raw suppliers

ADIBO-PEG4-acid 90% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: DBCO-PEG4-acid is an analog of DBCO-Acid with PEG linker and a DBCO group. The DBCO groups is commonly used for copper-free Click Chemistry reactions due to its strain promoted high energy. The hydrophilic PEG chain allows for increased water solubility. 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: Acid functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage. The PEG spacer adds hydrophilicity to the product to decrease aggregation.

Technology Process of DBCO-PEG4-Acid

There total 13 articles about DBCO-PEG4-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:

3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid (663921-15-1) + 4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-71-3) → 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid (1537170-85-6,2353410-00-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid (1353016-71-3) + 14-carboxy-3,6,9,12-tetraoxatetradecan-1-ammonium 2,2,2-trifluoroacetate (1615234-93-9) → 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid (1537170-85-6,2353410-00-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

Tetraethylene glycol (112-60-7) → 1-(4-{2-azatricyclo[10.4.0.04,9]hexadeca-1(12),4(9),5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oic acid (1537170-85-6,2353410-00-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium / tetrahydrofuran / 20 °C

1.2: 20 °C

2.1: triethylamine / dichloromethane / 3 h / Cooling with ice

3.1: sodium azide / N,N-dimethyl-formamide / 4 h / 80 °C

4.1: hydrogen; palladium 10% on activated carbon / methanol / 1 h / 20 °C

5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

6.1: triethylamine / N,N-dimethyl-formamide / 20 °C

With sodium azide; palladium 10% on activated carbon; hydrogen; sodium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

Tetraethylene glycol

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

tert-butyl 1-(methanesulfonyloxy)-3,6,9,12-tetraoxapentadecan-15-oate

tert-butyl 1-azido-3,6,9,12-tetraoxapentadecan-15-oate

Downstream raw materials:

2,5-dioxopyrrolidin-1-yl 1-(4-{2-azatricyclo[10.4.0.0^4,9]hexadeca-1⁽¹²⁾,4⁽⁹⁾,5,7,13,15-hexane-10-yn-2-yl}-4-oxobutanamido)-3,6,9,12-tetraoxapentadecan-15-oate