The use of iodotrimethylsilane in nucleosidation procedure.
1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (I) was reacted with iodotrimethylsilane (II) and the product, the glycosyl iodide, was coupled with silylated uracil to afford 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)uracil (III; 89%), with silyated cytosine to afford, on subsequent acetylation, 1-(2,3,5-tri-O-benzoyl-beta-0D-ribofuranosyl)-4-acetamido-2-(1H)-pyrimidinone (IVb; 81%), and with chloromercuri-N-benzoyl-adenine to afford Va and on subsequent debenzoylation, adenosine (Vb; 49%).
D000107:Acetylation; D055598:Chemical Phenomena; D002621:Chemistry; D007202:Indicators and Reagents; D008722:Methods; D009705:Nucleosides / Q000032:analysis*; D012825:Silicon; D013329:Structure-Activity Relationship; D014297:Trimethylsilyl Compounds
D007202:Indicators and Reagents; D009705:Nucleosides; D014297:Trimethylsilyl Compounds; C027752:iodotrimethylsilane; D012825:Silicon