Synthesis of unsaturated carboacyclic nucleoside analogues via Mitsunobu reactions.
2-Substituted allyl alcohols 9 and 14 were prepared starting from butane-1,2,4-triol and glycerol, respectively. Mitsunobu condensations of 9 and 14 with purine and pyrimidine bases, followed by deprotection, afforded a number of acyclonucleosides having 4-hydroxy-2-methylenebutyl or 3,3-bis(hydroxymethyl)-2-methylenepropyl chain.
Du
J
J
Chemistry Laboratory, ICN Pharmaceuticals, Inc., Costa Mesa, California 92626, USA.
Wang
G
G
D000475:Alkenes / Q000138:chemical synthesis*; D002073:Butanes / Q000138:chemical synthesis*; D018736:DNA Adducts / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D011407:Propane / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D011684:Purine Nucleosides / Q000138:chemical synthesis*; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis
C414826:3,3-bis(hydroxymethyl)-2-methylenepropyl; C414825:4-hydroxy-2-methylenebutyl; D000475:Alkenes; D002073:Butanes; D018736:DNA Adducts; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; D011407:Propane