期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 14, 期 -, 页码 2404-2410出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.217
关键词
click cyclization; conformation; macrocycles; nucleosides; X-ray
Copper(I)-promoted click cyclization in the presence of TBTA afforded nucleoside macrocycles in very high yields (approximate to 70%) without using protecting groups. To this end, dU and dC derivatives functionalized at the 5-position of the nucleobase with octadiynyl side chains and with azido groups at the 5'-position of the sugar moieties were synthesized. The macrocycles display freely accessible Watson-Crick recognition sites. The conformation of the 16-membered macrocycle was deduced from X-ray analysis and H-1, H-1-NMR coupling constants. The sugar conformation (N vs S) was different in solution as compared to the solid state.
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