[N,1-(15)N2]-2'-deoxyadenosines.
[reaction: see text] An efficient route to deoxyadenosine derivatives labeled on both the amino group and nitrogen 1 is uncovered. First, 3',5'-di-O-acetyl-2'-deoxy-1-(2-nitrobenzenesulfonyl)inosine (2a) and only 1.1 equiv of (15)NH4Cl are used for labeling position 1 (1a) through the isolation of the open intermediate and its cyclization with DBU in anhydrous CH3CN. Inosine 1a is then converted to [N,1-(15)N2]-3',5'-di-O-acetyl-N6-benzoyl-2'-deoxyadenosine (5a, the precursor of 6a) via a Pd/dppf-catalyzed chloride-to-benzamide replacement, by using again only 1.1 equiv of the labeling source.
Terrazas
Montserrat
M
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain.
Ariza
Xavier
X
Vilarrasa
Jaume
J
D002384:Catalysis; D003500:Cyclization; D003839:Deoxyadenosines / Q000138:chemical synthesis / Q000737:chemistry; D007288:Inosine / Q000737:chemistry; D015394:Molecular Structure; D009587:Nitrogen Isotopes; D010165:Palladium / Q000737:chemistry
D003839:Deoxyadenosines; D009587:Nitrogen Isotopes; D007288:Inosine; D010165:Palladium