Reaction #56599

ord-a30fca9873514a169f7249087f944381

Reaction equation

Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O
thymidine
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
→
Cc1cn2c(nc1=O)O[C@@H]1C[C@H]2O[C@@H]1CO
anhydrothymidine

Reactants

—
nucleoside
—
anhydronucleoside
Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]c1=O
thymidine
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
—
anhydronucleoside

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Dryingazeotropically drying with portions of acetonitrile (MeCN)
  2. 2
    Temperaturecooled
  3. 3
    workup.ADDITIONis added dropwise to the mixture
  4. 4
    workup.ADDITIONThe resulting mixture is treated with water
  5. 5
    Otherto form a suspension that
  6. 6
    Filtrationis filtered

Procedure

There are a variety of known techniques for converting a nucleoside into an anhydronucleoside. For example, the anhydronucleoside can be prepared by mixing thymidine with triphenylphosphine and azeotropically drying with portions of acetonitrile (MeCN). The resulting mass is suspended in MeCN and then cooled. The mixture is rapidly stirred and diisopropylazodicarcobxylate in MeCN is added dropwise to the mixture. The resulting mixture is treated with water to form a suspension that is filtered to afford anhydrothymidine. (Grierson, J. R., Shields, A. F., Nuclear Medicine and Biology, 2000, 27 143-156; Balagopala, M. I., Ollapally, A. P., and Lee, H. J., Nucleosides-Nucleotides, 1996, 15(4) 899-906).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419653B2uspto-grants-2008_09