Tos-PEG2-t-butyl ester

Base Information

• Chemical Name: Tos-PEG2-t-butyl ester
• CAS No.: 1309666-78-1
• Molecular Formula: C₁₆H₂₄O₆S
• Molecular Weight: 344.429
• Mol file: 1309666-78-1.mol

Synonyms:tert-butyl 3-[2-(4-methylphenyl)sulfonyloxyethoxy]propanoate

Chemical Property of Tos-PEG2-t-butyl ester

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Tos-PEG2-t-butylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Tos-PEG2-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.

Technology Process of Tos-PEG2-t-butyl ester

There total 3 articles about Tos-PEG2-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: 86.0%

p-toluenesulfonyl chloride (98-59-9) + 3-(2-hydroxyethoxy)propionic acid tert-butyl ester (671802-00-9,892154-71-1) → tert-butyl 3-[2-(4-methylphenyl)sulfonyloxyethoxy]propanoate (1309666-78-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at -10 - 20 ℃; for 8h;

DOI:10.1021/acsmedchemlett.9b00025

Reference yield: 56.0%

toluene-4-sulfonic acid (104-15-4) + 3-(2-hydroxyethoxy)propionic acid tert-butyl ester (671802-00-9,892154-71-1) → tert-butyl 3-[2-(4-methylphenyl)sulfonyloxyethoxy]propanoate (1309666-78-1)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1002/chem.201003285

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) → tert-butyl 3-[2-(4-methylphenyl)sulfonyloxyethoxy]propanoate (1309666-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

1.2: 48 h / 0 - 20 °C

2.1: triethylamine / tetrahydrofuran / 16 h / 0 - 20 °C

With sodium hydride; triethylamine; In tetrahydrofuran;

upstream raw materials:

toluene-4-sulfonic acid

3-(2-hydroxyethoxy)propionic acid tert-butyl ester

tert-Butyl acrylate

p-toluenesulfonyl chloride

Downstream raw materials:

C₄₄H₅₂O₈

3-(2-aminoethoxy)propionic acid tert-butyl ester