Preparation of 8,5'-O-cycloadenosine derivatives by reaction of 2',3'-O-isopropylideneadenosine with phenyl chloroformate or p-toluyl chloride.
Reaction of 2',3'-O-isopropylideneadenosine with p-toluyl chloride in a mixture of methylene chloride and triethylamine afforded 2',3'-O-isopropylidene-N,N,5'-O-tri-p-toluyladenosine (8)(30%), 8,5'-O-cycloadenosine derivatives 9 (34%) and 10 (11%), and a cyanoimidazole nucleoside 11 (12%).
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002723:Chlorobenzoates; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013329:Structure-Activity Relationship; D014050:Toluene / Q000031:analogs & derivatives
D002723:Chlorobenzoates; D007202:Indicators and Reagents; C014626:2',3'-isopropylideneadenosine; D014050:Toluene; C032544:phenyl chloroformate; D000241:Adenosine