A new method for the synthesis of N2-alkylguanosines using Mitsunobu reaction as a key step.
Peracetylated guanosine was reacted with POCl3 to give an 2-acetamido-6-chloro-9H-purine derivative, which was condensed with primary or secondary alcohols to give N2-alkylated analogues. The products were treated with mercaptoethanol in the presence of sodium methoxide to afford N2-alkylguanosines.
Kozai
S
S
Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan.
Yorikane
A
A
Maruyama
T
T
D002855:Chromatography, Thin Layer; D006151:Guanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008623:Mercaptoethanol / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
D006151:Guanosine; D008623:Mercaptoethanol; D000432:Methanol