PURINE NUCLEOSIDES .25. SYNTHESIS OF CERTAIN DERIVATIVES OF 5'-AMINO-5'-DEOXY- AND 5'-AMINO-2',5'-DIDEOXY-BETA-D-RIBOFURANOSYLPURINES AS PURINE NUCLEOTIDE ANALOGS

The 2′3′-O-isopropylidene-5′-amino-5′-deoxy nucleoside derivatives of adenosine (2a) and guanosine (2b) were isolated and characterized for the first time. The synthesis of 5′-amino-2′,5′-dideoxyadenosine (11) has now been accomplished by a similar route. Treatment of the 5′-amino purine nucleosides 2a, 2b, and 11 with MeSO2Cl provided the corresponding 5′-N-methanesulfonylamino purine nucleoside derivatives. Appropriate deblocking yielded 5′-N-methanesulfonylamino-5′-deoxyadenosine (6a), 5′-N-methanesulfonylammo-5′-deoxyguanosine (6b), and 5′-N-methanesulfonylamino-2′-5′-dideoxyadenosine (12), respectively. Similar reaction of the requisite 5′-amino purine nucleosides 2a, 2b, and 11 with ethyl chlorocarbonate followed by appropriate deblocking procedures gave 5′-N-ethoxycarbonylamino-5′-deoxyadenosine (5a), 5′-N-ethoxycarbonylamino-5′-deoxyguanosine (5b), and 5′-N-ethoxycarbonylamino-2′,5′-dideoxyadenosine (10), respectively. The rationale for consideration of these nucleoside derivatives as 5′-nucleotide analogs is presented and discussed. © 1969, American Chemical Society. All rights reserved.