t-Boc-N-Amido-PEG2-Azide

Base Information

• Chemical Name: t-Boc-N-Amido-PEG2-Azide
• CAS No.: 950683-55-3
• Molecular Formula: C11H22N4O4
• Molecular Weight: 274.32
• Mol file: 950683-55-3.mol

Synonyms:t-Boc-N-Amido-PEG2-Azide;Boc-N-Amido-PEG2-Azide

Chemical Property of t-Boc-N-Amido-PEG2-Azide

Chemical Property:

• PSA: 106.54000
• LogP: 1.69826

Purity/Quality:

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

t-Boc-N-Amido-PEG2-azide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: t-Boc-N-Amido-PEG2-azide is a PEG linker, which can react with alkyne, BCN, DBCO via Click Chemistry. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Technology Process of t-Boc-N-Amido-PEG2-Azide

There total 2 articles about t-Boc-N-Amido-PEG2-Azide 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:

2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol (6338-55-2) → {2-[2-(2-azidoethoxy)ethoxy]ethyl}carbamic acid tert-butyl ester (950683-55-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / methanol / 3 h / Reflux

2: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 4 h / 60 °C / Inert atmosphere

With sodium azide; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.09.124

Reference yield:

triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → {2-[2-(2-azidoethoxy)ethoxy]ethyl}carbamic acid tert-butyl ester (950683-55-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 80 °C

2: hydrogenchloride; triphenylphosphine / water; toluene / 16 h / 0 - 20 °C

3: triethylamine / dichloromethane / 0.83 h

With hydrogenchloride; sodium azide; tetra-(n-butyl)ammonium iodide; triethylamine; triphenylphosphine; In dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/cbic.201000280

Reference yield: 89.0%

{2-[2-(2-azidoethoxy)ethoxy]ethyl}carbamic acid tert-butyl ester (950683-55-3) + 5-(chloromethyl)-1,2,3-tris(prop-2-yn-1-yloxy)benzene (1061204-50-9) → C49H79ClN12O15

Guidance literature:

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In toluene; at 20 ℃;

DOI:10.1039/d0tb00113a

upstream raw materials:

triethylene glycol di-(p-toluenesulfonate)

2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol

Downstream raw materials:

1-{2-[2-(2-aminoethoxy)ethoxy]ethyl}-2,5-dihydro-1H-pyrrole-2,5-dione trifluoroacetate

C₃₁H₃₅BF₂N₄O₆

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

(S)-2-{2-[2-(tert-butoxycarbonylamino)ethoxy]ethoxy}ethyl 2-((2S,3R)-3-{[(9H-fluoren-9-yl)methoxy]carbonylamino}-2-hydroxy-4-phenyl-butanamido)-4-methylpentanamide

Refernces

• 1、 -. "IRAK DEGRADERS AND USES THEREOF". . . Retrieved 2019/07/10.
• 2、 Willems, Lianne I.,Verdoes, Martijn,Florea, Bogdan I.,Van Der Marel, Gijsbert A.,Overkleeft, Herman S.. "Two-step labeling of endogenous enzymatic activities by Diels-Alder ligation". . p. 1769 - 1781. Retrieved 2011/04/18.