Abstract
A simple and convenient methodology has been developed for the synthesis of novel hexopyranosyl pyrimidine homonucleosides and hexopyranosyl double-headed pyrimidine homonucleosides from the corresponding native sugars, d-glucose and d-mannose. Thus, hexose sugars were converted to 2,6-anhydro-3,4,5,7-tetra-O-benzyl-heptitols and 2,6-anhydro-3,4,5-tri-O-benzyl-heptitols by recently developed procedure of Khatri et al. Further, mono- and di-hydroxy 2,6-anhydro-heptitols were converted to their corresponding mono- and di-tosylated derivatives, which were then translated into hexopyranosyl homonucleosides and double-headed homonucleosides by reaction with uracil and thymine in 40–50 and 27–73% overall yields from tetra- and tri-O-benzylated anhydro-heptitols.
Graphical Abstract
Acknowledgments
We are thankful to CIF-USIC, University of Delhi, for providing NMR spectral and HRMS recording facility.