Tos-PEG3-t-butyl ester

Base Information

• Chemical Name: Tos-PEG3-t-butyl ester
• CAS No.: 850090-13-0
• Molecular Formula: C18H28O7S
• Molecular Weight: 388.482

Synonyms:9-(p-toluenesulfonyloxy)-4,7-dioxanonanoic acid tert-butyl ester;3-{2-[2-(Toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester;tert-butyl 3-(2-(2-(tosyloxy)ethoxy)ethoxy)propanoate;

Chemical Property of Tos-PEG3-t-butyl ester

Chemical Property:

• Boiling Point: 495.2±35.0 °C(Predicted)
• PSA: 96.51000
• Density: 1.159±0.06 g/cm3(Predicted)
• LogP: 3.54610

Purity/Quality:

98% ^*data from raw suppliers

3-{2-[2-(Toluene-4-sulfonyloxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Tos-PEG3-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-PEG3-t-butyl ester

There total 4 articles about Tos-PEG3-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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + 2-methyl-2-propanyl 3-[2-(2-hydroxyethoxy)ethoxy]propanoate (133803-81-3,892154-71-1) → 9-(p-toluenesulfonyloxy)-3,6-diocanonanoic acid tert-butyl ester (850090-13-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1002/cbic.202100243

Reference yield: 61.3%

2-methyl-2-propanyl 3-[2-(2-hydroxyethoxy)ethoxy]propanoate (133803-81-3,892154-71-1) → 9-(p-toluenesulfonyloxy)-3,6-diocanonanoic acid tert-butyl ester (850090-13-0)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20 ℃;

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) → 9-(p-toluenesulfonyloxy)-3,6-diocanonanoic acid tert-butyl ester (850090-13-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium / tetrahydrofuran / 16 h / 20 - 40 °C / Inert atmosphere

2: pyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium; In tetrahydrofuran; dichloromethane; 1: |Michael Addition;

DOI:10.1002/ejoc.201300236

upstream raw materials:

p-toluenesulfonyl chloride

2-methyl-2-propanyl 3-[2-(2-hydroxyethoxy)ethoxy]propanoate

tert-Butyl acrylate

Downstream raw materials:

3-(2-(2-azidoethoxy)ethoxy)propanoic acid

tert-butyl 3-(2-(2-azidoethoxy)ethoxy)propanoate

2-methyl-2-propanyl 3-[2-(2-aminoethoxy)ethoxy]propanoate

3-(2-{2-[3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido]ethoxy}ethoxy)propanoic acid

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