Reaction of 2'5'-dichloro-2'5'-dideoxyuridine with nucleophiles.
Reaction of 2',5'-dichlorouridine (1) with amines and thiols afforded 2-N-substituted 2',5'-anhydroisocytidine derivatives (2) and 2,2'-anhydro-5'-thiouridine derivatives (5), respectively. When 2,2'-anhydro-5'-acetylthiouridine (5a) was treated with NaOMe, 3',5'-S-cyclouridine (6) was obtained.
D000588:Amines; D000641:Ammonia; D055598:Chemical Phenomena; D002621:Chemistry; D003857:Deoxyuridine / Q000031:analogs & derivatives*; D015224:Dideoxynucleosides; D013329:Structure-Activity Relationship; D014529:Uridine / Q000031:analogs & derivatives*
D000588:Amines; D015224:Dideoxynucleosides; C047920:2',5'-dichloro-2',5'-dideoxyuridine; D000641:Ammonia; D003857:Deoxyuridine; D014529:Uridine