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Syntheses and hydrolysis reactions of some 2 3' substituted imino 1 3' deoxy beta d lyxofuranosyluracils



Syntheses and hydrolysis reactions of some 2 3' substituted imino 1 3' deoxy beta d lyxofuranosyluracils



Journal of Organic Chemistry 51(23): 4417-4424



With a view to examining the possibility of "up" amination of the sugar moiety of pyrimidine furanosyl nucleosides through pyrimidine N-cyclonucleosides, variously N-substituted derivatives of 2,3'-imino-1-(3'-deoxy-.beta.-D-lyxofuranosyl)uracil (3c)3a (3a,b and 3d-h) were synthesized through their 5'-O-benzoyl precursors (2a,b and 2d-h), which in turn were obtained from 2,2'-anhydro uracil nucleosides (1)7 and excess amounts of various amines. 2a and 2b are oxidatively convertible into 3c. Alkaline hydrolysis of 3b, 3d, and 3e with 6 N NaOH/EtOH (1:1) gave the corresponding N-bridged lyxopyranosyl nucleosides 4a-c, while the similar treatments of the N-aryl analogues 3f,g gave the corresponding lyxopyranosyl isomers 4d,e as well as the "up" arylamino nucleosides 5a,b in similar yields in each case. The parent compound 4f was prepared from 4a. Some spectroscopic and mechanistic arguments on the formation and structures of the products are also given.

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