Development of new dihydropyran linker for solid-phase reaction.
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 delta-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 degrees 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.
Ryu
J H
JH
Department of Pharmaceutical Sciences, College of Pharmacy, Kyung Hee University, Seoul, Korea.
Jeong
J H
JH
D000438:Alcohols / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004341:Drug Evaluation / Q000379:methods; D011714:Pyrans / Q000138:chemical synthesis*; D012116:Resins, Plant / Q000737:chemistry
D000438:Alcohols; D002241:Carbohydrates; D011714:Pyrans; D012116:Resins, Plant