Development of new dihydropyran linker for solid-phase reaction

The linker which plays a role in connecting a polymer with a scaffold has b ecome an important part in solid-phase reaction. To develop a new linker fo r alcohols and carbohydrates, dihydropyran moiety was selected in this stud y. New linker, 1-(4',5'-dihydro-5H-pyranyl)-7-hydroxyheptan-3-one (5) was synt hesized 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. Carboh ydrate and hydroxyl resins were connected via new linker in a 70% loading y ield. The detachment of glucose moiety in the presence of PPTS (2 equiv.) i n 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 fac t is particularly very important in industry, because recovered resins can be recycled.