Nucleoside Analogues with a Novel Glycone Based on the Benzo[C]Furan Core

Abstract

Listen

Translate article

Routes to novel nucleoside analogues based on 1, 3-dihydrobenzo[c]furan have been investigated. Thus l-(1, 3-dihydro-3-hydroxymethylbenzo[c]furan-1-yl)-thymine, an analogue of d4T, was obtained as two diastereoisomers. The cis compound (quasi β-D/α-L stereochemistry) was obtained pure but the trans compound was only 90% pure. A purine analogue with a four atom spacer group between base and glycone was also prepared. The conformation of these constrained nucleosides was studied by molecular modelling.