Abstract

An efficient synthetic method has been developed for the synthesis of 2′-deoxyguanosine from the more commercially available 2′-deoxyadenosine via late-stage C2 nitration in 48.7% total yield by a 5-step synthetic procedure. Crucially, 2′-deoxyadenosine was fully protected by bennzoyl groups and then nitrated at C2 by tetrabutylammonium nitrate/trifluoroacetic anhydride. The resulting 2-NO₂ moiety was converted into 2-NH₂ by Ni-catalyzed hydrogenolysis. Finally, 2′-deoxyguanosine was obtained from the diaminopurine intermediate by deaminase-catalyzed reaction. Furthermore, the 2-NO₂ moiety also appeared to be a versatile handle to introduce a variety of functional groups, resulting in a divergent access to 2-substituted 2′-deoxyadenosine analogues.

摘要

已经开发了一种有效的合成方法，用于通过 5 步合成程序通过后期 C2 硝化以 48.7% 的总产率从更商业化的 2'-脱氧腺苷合成 2'-脱氧鸟苷。至关重要的是，2'-脱氧腺苷被苯甲酰基完全保护，然后在 C2 处被四丁基硝酸铵/三氟乙酸酐硝化。所得2-NO ₂部分通过Ni催化氢解转化为2-NH _{2 。}最后，通过脱氨酶催化反应从二氨基嘌呤中间体获得2'-脱氧鸟苷。此外，2-NO ₂moiety 似乎也是一个通用的手柄，可以引入各种官能团，导致对 2-取代的 2'-脱氧腺苷类似物的不同访问。