Synthesis and properties of 2'-deoxy-8,2'-methylene-cyclopurine nucleosides.
A method was developed to synthesize 2'-deoxy-8,2'-methylene-cycloadenosine (1) and -cycloguanosine (2) which were new carbon-bridged cyclopurine nucleosides fixed in a high-anti torsional angle region. 3',5'-Di-O-acetyl-8-methanesulfonyl-2'-O-p-toluene-sulfonyladenosine+  ++ (3) or 2-acetamido-9- (3,5-di-O-acetyl-2-O-p-toluenesulfonyl-beta-D-ribofuranosyl)-6- ethoxy-8-methanesulfonyl-purine (9) was treated with sodium salt of ethyl malonate to give the cyclized nucleosides (4 and 10) in good yields, respectively. Subsequent decarboxylation and deblocking of 4 and 10 afforded 1 and 2 in crystalline form, respectively.
D055598:Chemical Phenomena; D002621:Chemistry; D003839:Deoxyadenosines / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents; D008968:Molecular Conformation; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D003839:Deoxyadenosines; D007202:Indicators and Reagents; D011684:Purine Nucleosides; C044277:2'-deoxy-8,2'-methylene-cycloadenosine; C044278:2'-deoxy-8,2'-methylene-cycloguanosine; D003849:Deoxyguanosine