Synthesis of Nucleoside Libraries on Solid Support. II. 2,6,8‐Trisubstituted Purine Nucleosides Using 8‐Bromoguanosine as Precursor

Abstract

A series of 2,6,8‐trisubstituted purine nucleoside libraries was prepared by parallel solid‐phase synthesis using 8‐bromoguanosine as a common synthetic precursor. Polystyrene‐methoxytrityl chloride resin was linked to the N² or O5′ position of the guanosine analogues. 8‐Bromoguanosine was derivatized at the C8 position via carbon‐carbon bond formation. Nucleophilic aromatic substitution at C2 and/or C6 positions with various amines produced two series of purine nucleoside libraries with very diverse substitution.

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

Keywords:

• Combinatorial library
• Nucleoside
• Purine

Notes

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.