Azide-PEG3-Tos

Base Information

• Chemical Name: Azide-PEG3-Tos
• CAS No.: 178685-33-1
• Molecular Formula: C13H19N3O5S
• Molecular Weight: 329.377
• Mol file: 178685-33-1.mol

Synonyms:2-(2-(2-azidoethoxy)ethoxy)ethyl tosylate;toluene 4-sulfonic acid 2-[2-(2-azidoethoxy)ethoxy] ethyl ester;2-(2-(2-azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate;2-[2-(2-azidoethoxy)ethoxy]ethyl 4-methylbenzenesulfonate;2-(2-(2-azidoethoxy)ethoxy)ethyl toluenesulfonate;Toluene-4-sulfonic acid 2-[2-(2-azido-ethoxy)-ethoxy]-ethyl ester;α-azidodeoxy-ω-O-tosyltriethyleneglycol;

Chemical Property of Azide-PEG3-Tos

Chemical Property:

• PSA: 119.96000
• LogP: 2.57736
• Solubility.: Soluble in DMSO, DCM, DMF

Purity/Quality:

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

2-(2-(2-Azidoethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Azide-PEG3-Tos is a heterobifunctional PEG linker.The azide (N3) group is reactive with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. Tosyl group is a good leaving group for nucleophilic substitution reactions.

Technology Process of Azide-PEG3-Tos

There total 10 articles about Azide-PEG3-Tos 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%

2-[2-(2-azidoethoxy)ethoxy]ethanol (86520-52-7) + p-toluenesulfonyl chloride (98-59-9) → 8-azido-3,6-dioxaoctyl tosylate (178685-33-1)

Guidance literature:

With triethylamine;

DOI:10.1016/j.bmcl.2009.01.028

Reference yield: 94.0%

2-[2-(chloroethoxy)ethoxy]ethanol (5197-62-6) + p-toluenesulfonyl chloride (98-59-9) → 8-azido-3,6-dioxaoctyl tosylate (178685-33-1)

Guidance literature:

2-[2-(chloroethoxy)ethoxy]ethanol; With sodium azide; sodium iodide; In water; at 80 ℃; for 18h;

p-toluenesulfonyl chloride; With triethylamine; dmap; at 20 ℃; for 18h;

Reference yield: 90.0%

p-toluenesulfonyl chloride (98-59-9) → 8-azido-3,6-dioxaoctyl tosylate (178685-33-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; water; ethyl acetate;

upstream raw materials:

triethylene glycol di-(p-toluenesulfonate)

p-toluenesulfonyl chloride

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

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

Downstream raw materials:

C₁₉H₂₄F₄N₄O₈S

(8S,9R,11S,13S,14S)-11-(4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenyl)-7,8,9,11,12,13,14,15,16,17-decahydro-13-methyl-17-oxo-6H-cyclopenta[a]phenanthren-3-yl acetate

(8S,9R,11S,13S,14S)-11-(4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenyl)-7,8,9,11,12,13,15,16-octahydro-3-hydroxy-13-methyl-6hcyclopenta[a]phenanthren-17(14H)-one

11β-(4-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)phenyl)estra-1,3,5(10)-triene-3,17β-diol

Refernces

• 1、 Xu, Duo,Peng, Chenyu,Gao, Fei,Guo, Zhide,Zhuang, Rongqiang,Su, Xinhui,Zhang, Xianzhong. "Radioiodinated estradiol dimer for estrogen receptor targeted breast cancer imaging". . p. 1332 - 1340. Retrieved 2020.
• 2、 Raddaoui, Nada,Stazzoni, Samuele,M?ckl, Leonhard,Viverge, Bastien,Geiger, Florian,Engelke, Hanna,Br?uchle, Christoph,Carell, Thomas. "Dendrimer-Based Signal Amplification of Click-Labelled DNA in Situ". . p. 1716 - 1720. Retrieved 2017.
• 3、 Patel, Kaushik,Angelos, Sarah,Dichtel, William R.,Coskun, Ali,Yang, Ying-Wei,Zink, Jeffrey I.,Stoddart, J. Fraser. "Enzyme-responsive snap-top covered silica nanocontainers". . p. 2382 - 2383. Retrieved 2008.
• 4、 -. "Compound for inducing Tau protein degradation based on CRBN ligand as well as preparation method, pharmaceutical composition and application of compound". Paragraph 0058-0060. . Retrieved 2021/08/28.
• 5、 Wang, Yuqi,Weng, Jianhui,Ye, Deju,Zhang, Yan. "An Activatable Near-Infrared Fluorescence Probe for in Vivo Imaging of Acute Kidney Injury by Targeting Phosphatidylserine and Caspase-3". . p. 18294 - 18304. Retrieved 2021/11/10.