Premium
Solid‐Phase Microwave‐Assisted Ligand‐Free Suzuki‐Miyaura Cross‐Coupling of 5‐Iodouridine
Author(s) -
Patel Bhautikkumar,
Zunk Dr Matthew,
Grant Dr Gary,
Rudrawar Santosh
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201703111
Subject(s) - chemistry , moiety , linker , ligand (biochemistry) , combinatorial chemistry , aryl , nucleobase , acetal , nucleoside , uridine , stereochemistry , organic chemistry , rna , dna , biochemistry , alkyl , receptor , computer science , gene , operating system
A soild‐supported 5‐iodouridine derivative underwent Suzuki‐Miyaura cross‐coupling reactions with various aryl/heteroarylboronic acids under microwave‐assisted ligand‐free conditions yielding 5‐aryl/heteroaryl uridine derivatives. Reactions were performed using Pd(dppf)Cl 2 ⋅ CH 2 Cl 2 as catalyst and K 3 PO 4 as base in a tert ‐BuOH/toluene/water solvent system. In our synthetic strategy uridine nucleosides were anchored onto 2‐chlorotrityl chloride resin through an acetal linkage blocking the 2′ – and 3′ –OH of the ribose moiety thus allowing an enormous opportunity for modifications on the nucleobase or on the 5′‐position. The described method offers an acid labile acetal linker strategy thus allowing potential application in Fmoc‐Solid‐Phase Peptide Synthesis or late stage modification of uridyl peptide nucleoside antibiotic analogues synthesis.