Synthesis of 1,2-unsaturated pyranosylphosphonate nucleosides from 3,4,6-tri-O-acetyl-D-glycal.

@article{Ismail2001SynthesisO1,
  title={Synthesis of 1,2-unsaturated pyranosylphosphonate nucleosides from 3,4,6-tri-O-acetyl-D-glycal.},
  author={Ahmad Zaki Hj. Ismail},
  journal={Die Pharmazie},
  year={2001},
  volume={56 7},
  pages={534-5}
}
Ferrier rearrangement of 3,4,6-tri-O-acetyl-D-glucal (1) in the presence of triethylphosphite afforded the 2,3-unsaturated pyranose 2. Deacetylation and simultaneous migration of the double bond to 1,2-position in the sugar moiety was achieved by stirring in sodium ethoxide. Tosylation with one equivalent of tosyl chloride afforded 4. Nucleophile… CONTINUE READING