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Development of new dihydropyran linker for solid-phase reaction
1Department of Pharmaceutical Sciences, College of Pharmacy, Kyung Hee University, Seoul, Korea.
Archives of Pharmacal Research
|January 1, 2000
Summary
A novel dihydropyran linker was synthesized for solid-phase reactions, enabling efficient attachment and quantitative release of carbohydrates and alcohols. This linker allows for the recovery and recycling of Wang resin, crucial for industrial applications.
Area of Science:
- Organic Chemistry
- Polymer Chemistry
- Solid-Phase Synthesis
Background:
- Linkers are essential for connecting polymers to scaffolds in solid-phase reactions.
- Developing efficient linkers is key for advancing combinatorial chemistry and material science.
Purpose of the Study:
- To synthesize a novel dihydropyran-based linker for attaching alcohols and carbohydrates to solid supports.
- To evaluate the linker's efficiency in loading, release, and resin recyclability.
Main Methods:
- A four-step synthesis of the dihydropyran linker (1-(4',5'-dihydro-5H-pyranyl)-7-hydroxyheptan-3-one) from delta-valerolactone.
- Attachment of Wang resin to one pyran ring and subsequent coupling of alcohols/carbohydrates to the other.
- Quantitative release of glucose moiety using pyridinium p-toluenesulfonate (PPTS) under specific conditions.
Main Results:
- The novel dihydropyran linker was successfully synthesized and functionalized with Wang resin.
- Carbohydrates and hydroxyl groups were attached to the linker with a 70% loading yield.
- Quantitative release of glucose was achieved, and the Wang resin was recovered for potential recycling.
Conclusions:
- The developed dihydropyran linker provides an effective method for solid-phase attachment and release of alcohols and carbohydrates.
- The ability to recover and recycle the Wang resin offers significant advantages for industrial-scale chemical synthesis.