反応 #56599

ord-a30fca9873514a169f7249087f944381

反応方程式

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

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    乾燥azeotropically drying with portions of acetonitrile (MeCN)
  2. 2
    温度cooled
  3. 3
    workup.ADDITIONis added dropwise to the mixture
  4. 4
    workup.ADDITIONThe resulting mixture is treated with water
  5. 5
    その他to form a suspension that
  6. 6
    ろ過is filtered

実験手順

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).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07419653B2uspto-grants-2008_09