Synthesis of hexopyranosyl pyrimidine homonucleosides

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

Keywords:

• 2,6-Anhydro-heptitols
• hexopyranosyl double-headed homonucleosides
• hexopyranosyl homonucleosides
• hexopyranosyl pyrimidine homonucleosides

Acknowledgments

We are thankful to CIF-USIC, University of Delhi, for providing NMR spectral and HRMS recording facility.

Additional information

Funding

We are grateful to the University of Delhi for providing financial support under DU-DST Purse grant. V.V., V.K.M. thanks CSIR, New Delhi and CFEES (DRDO), New Delhi, for the award of Junior/Senior Research Fellowship, respectively.