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 language | English |
|---|---|
| Pages (from-to) | 585-591 |
| Number of pages | 7 |
| Journal | Archives of pharmacal research |
| Volume | 22 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 1999 Jan 1 |
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All Science Journal Classification (ASJC) codes
- Molecular Medicine
- Drug Discovery
- Organic Chemistry
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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 journal › Article
TY - JOUR
T1 - Development of new dihydropyran linker for solid-phase reaction
AU - Ryu, Joon Hyung
AU - Jeong, Jin-Hyun
PY - 1999/1/1
Y1 - 1999/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0033255902&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033255902&partnerID=8YFLogxK
U2 - 10.1007/BF02975331
DO - 10.1007/BF02975331
M3 - Article
C2 - 10615865
AN - SCOPUS:0033255902
VL - 22
SP - 585
EP - 591
JO - Archives of Pharmacal Research
JF - Archives of Pharmacal Research
SN - 0253-6269
IS - 6
ER -