85879-01-2Relevant academic research and scientific papers
Synthesis of Homo-C-nucleosides using Pyrimidinylmethylenephosphoranes
Katagiri, Nobuya,Takashima, Kenichi,Kato, Tetsuzo,Sato, Sadao,Tamura, Chihiro
, p. 201 - 209 (2007/10/02)
The direct synthesis of homo-C-nucleosides from pyrimidinylmethylenephosphoranes and protected D-ribose is described.Reaction of 2,3-O-isopropylidene-5-O-trityl-D-ribose (9) with pyrimidinylmethylenephosphoranes (5)-(8) gave protected α-and β-homo-C-nucleosides (14)-(21) and pyrimidinylolefins (10)-(13) in good yields.The ratio of α- and β-nucleosides depended on the properties of phosphoranes.Treatment of compounds (10)-(13) with base such as triethylamine or 1,8-diazabicycloundec-7-ene (DBU) gave ring-closed products (14)-(21) in quantitative yields.Deprotection of compounds (14)-(21) with hydrochloric acid in either dioxane-water or methanol gave homo-C-nucleosides (22)-(32).
