85878-89-3

Upstream product

• 54503-64-9 2,3-O-isopropylidene-5-O-trityl-D-ribofuranose 
• 85878-86-0 (6-chloro-2-methylpyrimidin-4-yl)methylenetriphenylphosphorane 
• 85878-91-7 Z-4-chloro-6-(1',2'-dideoxy-5'-hydroxy-3',4'-O-isopropylidene-6'-O-trityl-D-ribo-hex-1'-enyl)-2-methylpyrimidine 
• 85878-85-9 4-chloro-6-(chloromethyl)-2-methylpyrimidine 
• 74181-44-5 triphenylphosphorane 

Relevant academic research and scientific papers

Synthesis of Homo-C-nucleosides using Pyrimidinylmethylenephosphoranes

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).