Tos-PEG7-CH2CO2t-butyl ester

Base Information

• Chemical Name: Tos-PEG7-CH2CO2t-butyl ester
• CAS No.: 1530777-90-2
• Molecular Formula: C₂₅H₄₂O₁₁S
• Molecular Weight: 550.668
• Mol file: 1530777-90-2.mol

Synonyms:

Chemical Property of Tos-PEG7-CH2CO2t-butyl ester

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Tos-PEG7-CH2CO2tBu 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Tos-PEG7-CH2CO2tBu 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-PEG7-CH2CO2t-butyl ester

There total 9 articles about Tos-PEG7-CH2CO2t-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: 92.0%

p-toluenesulfonyl chloride (98-59-9) + tert-butyl 20-hydroxy-3,6,9,12,15,18-hexaoxaicosanoate (297162-47-1) → tert-butyl 20-(tosyloxy)-3,6,9,12,15,18-hexaoxicosanoate (1530777-90-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield:

pentaethylene glycol (2615-15-8) + t-butyl diazoacetate (35059-50-8) + p-toluenesulfonyl chloride (98-59-9) → tert-butyl 20-(tosyloxy)-3,6,9,12,15,18-hexaoxicosanoate (1530777-90-2)

Guidance literature:

pentaethylene glycol; t-butyl diazoacetate; With boron trifluoride diethyl etherate; In dichloromethane; for 1.25h;

p-toluenesulfonyl chloride; With trimethylamine hydrochloride; triethylamine; In dichloromethane; for 1h; Further stages.;

DOI:10.1002/chem.200204304

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) → tert-butyl 20-(tosyloxy)-3,6,9,12,15,18-hexaoxicosanoate (1530777-90-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 20 °C

With dmap; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.7b00635

upstream raw materials:

pentaethylene glycol

t-butyl diazoacetate

p-toluenesulfonyl chloride

tert-butyl 20-hydroxy-3,6,9,12,15,18-hexaoxaicosanoate

Downstream raw materials:

tert-butyl 20-azido-3,6,9,12,15,18-hexaoxaeicosanoate

20-amino-3,6,9,12,15,18-hexaoxaeicosanoic acid tert-butyl ester

20-(fluoren-9-ylmethyloxycarbonylamino)-3,6,9,12,15,18-hexaoxaeicosanoic acid