Tos-PEG5 t-butyl ester

Base Information

• Chemical Name: Tos-PEG5 t-butyl ester
• CAS No.: 581065-94-3
• Molecular Formula: C22H36O9S
• Molecular Weight: 476.588
• Mol file: 581065-94-3.mol

Synonyms:

Chemical Property of Tos-PEG5 t-butyl ester

Chemical Property:

• Refractive Index: 1.49
• Boiling Point: 560.5±50.0 °C(Predicted)
• PSA: 114.97000
• Density: 1.151±0.06 g/cm3(Predicted)
• LogP: 3.57930

Purity/Quality:

99%+, ^*data from raw suppliers

tert-Butyl 1-(Tosyloxy)-3,6,9,12-tetraoxapentadecan-15-oate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Tos-PEG5-t-butyl ester is a PEG linker containing a t-butyl ester and a tosyl group. The hydrophilic PEG spacer increases solubility in aqueous media. The t-butyl protected carboxyl group can be deprotected under acidic conditions. The tosyl group is a very good leaving group for nucleophilic substitution reactions.
• Uses: This compound is used in preparation of taxanes. Taxanes have improved its toxicity and solubility in aqueous solution compared to paciitaxel.

Technology Process of Tos-PEG5 t-butyl ester

There total 6 articles about Tos-PEG5 t-butyl ester 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: 97.0%

p-toluenesulfonyl chloride (98-59-9) + tert-butyl 3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)propanoate (518044-32-1,892154-71-1) → tert-butyl 3-[2-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]ethoxy}ethoxy)ethoxy]propionate (581065-94-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Cooling with ice;

Reference yield:

Toluene-2-sulfonyl chloride (133-59-5) + tert-butyl 3-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)propanoate (518044-32-1,892154-71-1) → tert-butyl 3-[2-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]ethoxy}ethoxy)ethoxy]propionate (581065-94-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 48h;

Reference yield:

Tetraethylene glycol (112-60-7) → tert-butyl 3-[2-(2-{2-[2-(toluene-4-sulfonyloxy)-ethoxy]ethoxy}ethoxy)ethoxy]propionate (581065-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Na / tetrahydrofuran

1.2: 78 percent / tetrahydrofuran / 20 h / 20 °C

2.1: 80 percent / Et₃N / acetonitrile / 5 h / 20 °C

With sodium; triethylamine; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jm049705s

upstream raw materials:

p-toluenesulfonyl chloride

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

Tetraethylene glycol

tert-Butyl acrylate

Downstream raw materials:

tert-butyl 3-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethoxy]propanoate

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

C₂HF₃O₂*C₅₅H₉₆N₆O₁₃

C₅₁H₈₈N₆O₁₃*ClH

Refernces

• 1、 -. "USES OF ANTI-CD3 ANTIBODY FOLATE BIOCONJUGATES". Paragraph 00357; 00359. . Retrieved 2021/09/03.
• 2、 -. "ANTI-CD3 ANTIBODY FOLATE BIOCONJUGATES AND THEIR USES". Paragraph 00338; 00349; 00351. . Retrieved 2020/03/23.