期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 38, 页码 15013-15017出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b08273
关键词
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资金
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [EXC-2193/1-390951807]
- HFSPO (Human Frontier Science Program) [RGP0025/2016]
Phosphoramidite analogues of modified cyclotriphosphates provide a general and step-economical synthesis of nucleoside triphosphates and analogues on scale without the need for protecting groups. These reagents enable rapid access to pure nucleoside oligophosphates and a range of other analogues that were previously difficult to obtain (e.g., NH, CH2, CCl2, and CF2, replacements for O, phosphono- and phosphoimidazolides, -morpholidates, -azidates, and -fluoridates). DFT calculations demonstrate that the selectivity of the cyclotriphosphate opening reactions proceeds via an inline substitution mechanism that displaces the least charged leaving group.
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