THP-PEG8-Tos

Base Information

• Chemical Name: THP-PEG8-Tos
• CAS No.: 669556-37-0
• Molecular Formula: C24H40O10S
• Molecular Weight: 520.642
• Mol file: 669556-37-0.mol

Synonyms:17-[(tetrahydro-2H-pyran-2-yl)oxy]-1-tosyloxy-3,6,9,12,15-pentaoxaheptadecane;1-(2H-tetrahydropyran-2-yloxy)-17-tosyloxy-3,6,9,12,15-pentaoxaheptadecane;

Chemical Property of THP-PEG8-Tos

Chemical Property:

• PSA: 116.36000
• LogP: 3.40730
• Solubility.: Soluble in DMSO, DCM, DMF

Purity/Quality:

NLT 98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: THP-PEG7-Tos is a PEG linker with a THP protecting group and a tosyl moiety. The THP is an alcohol protecting group that can be removed under acidic conditions. The tosyl group is a very good leaving group for nucleophilic substitution reactions. The hydrophilic PEG linker increases the water solubility of the compound in aqueous media.

Technology Process of THP-PEG8-Tos

There total 11 articles about THP-PEG8-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: 100.0%

3,4-dihydro-2H-pyran (110-87-2) + toluene-4-sulfonic acid 2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester (42749-28-0) → 17-(tetrahydro-2H-pyran-2-yloxy)-3,6,9,12,15-pentaoxaheptadecyl 4-methylbenzenesulfonate (669556-37-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1039/b701438d

Reference yield: 85.0%

17-(2H-tetrahydropyran-2'-yloxy)-3,6,9,12,15-pentaoxaheptadecan-1-ol (42607-87-4) + p-toluenesulfonyl chloride (98-59-9) → 17-(tetrahydro-2H-pyran-2-yloxy)-3,6,9,12,15-pentaoxaheptadecyl 4-methylbenzenesulfonate (669556-37-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo035042v

Reference yield:

pentaethylene glycol (2615-15-8) → 17-(tetrahydro-2H-pyran-2-yloxy)-3,6,9,12,15-pentaoxaheptadecyl 4-methylbenzenesulfonate (669556-37-0)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂

With triethylamine; In dichloromethane;

DOI:10.1021/ma0487554

upstream raw materials:

2-(2-tetrahydropyran-2-yloxyethanoxy)ethanol

tetraethylene glycol di(p-toluenesulfonate)

3,4-dihydro-2H-pyran

toluene-4-sulfonic acid 2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester

Downstream raw materials:

17-azido-3,6,9,12,15-pentaoxaheptadecan-1-ol

2-{2-[2-(2-{2-[2-(2-{2-[2-(2-benzyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-tetrahydro-pyran

nonaethylene glycol

26-(phenylmethyloxy)-3,6,9,12,15,18,21,24-octaoxahexaeicosan-1-ol

Refernces

• 1、 Tichy, Tomá?,Andrei, Graciela,Dra?ínsky, Martin,Holy, Antonín,Balzarini, Jan,Snoeck, Robert,Kre?merová, Marcela. "New prodrugs of Adefovir and Cidofovir". experimental part. p. 3527 - 3539. Retrieved 2011/07/09.
• 2、 Taniguchi, Ikuo,Mayes, Anne M.,Chan, Eugene W. L.,Griffith, Linda G.. "A chemoselective approach to grafting biodegradable polyesters". . p. 216 - 219. Retrieved 2007/10/03.