Development of new dihydropyran linker for solid-phase reaction

Joon Hyung Ryu, Jin-Hyun Jeong

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The linker which plays a role in connecting a polymer with a scaffold has become an important part in solid-phase reaction. To develop a new linker for alcohols and carbohydrates, dihydropyran moiety was selected in this study. New linker, 1-(4′,5′-dihydro-5H-pyranyl)-7-hydroxyheptan-3-one (5) was synthesized via four steps from δ-valerolactone. This can be called as DDHP-linked Wang resin due to double dihy-dropyran rings. To the one pyran ring of new linker 5 was added Wang resin and other alcohols and carbohydrates as scaffolds were then added successfully to the another pyran ring. Carbohydrate and hydroxyl resins were connected via new linker in a 70% loading yield. The detachment of glucose moiety in the presence of PPTS (2 equiv.) in 1:1 n-butanol/1,2-dichloroethane at 60°C for 12 h was carried out quantitatively. When certain combinatorial chemical works are carried out using this dihydropyran linker, Wang resin itself can be recovered. Its fact is particularly very important in industry, because recovered resins can be recycled.

Original languageEnglish
Pages (from-to)585-591
Number of pages7
JournalArchives of pharmacal research
Volume22
Issue number6
DOIs
Publication statusPublished - 1999 Jan 1

Fingerprint

Pyrans
1-Butanol
Carbohydrates
Scaffolds
Resins
Alcohols
Hydroxyl Radical
Industry
Polymers
Glucose
Wang resin
ethylene dichloride

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery
  • Organic Chemistry

Cite this

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Development of new dihydropyran linker for solid-phase reaction. / Ryu, Joon Hyung; Jeong, Jin-Hyun.

In: Archives of pharmacal research, Vol. 22, No. 6, 01.01.1999, p. 585-591.

Research output: Contribution to journalArticle

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