Chinese Journal of Organic Chemistry >
Synthesis of 3'-Azido-D/L-nucleosides
Received date: 2017-08-02
Revised date: 2017-10-24
Online published: 2017-10-31
Supported by
Project supported by the Key Overseas Chinese Entrepreneurial Team Grant, Awarded by Overseas Chinese Affairs Office of the State Council.
Two orthorganally protected 3'-azido-3'-deoxy-D/L-ribosides were synthesized and successfully glycosylated with various pyrimidine, pyridine and purine related heterocyclic bases. 3'-Azido-3'-deoxy-D-pyrimidine nucleosides, purine nucleosides as well as 3'-azido-3'-deoxy-L-nucleosides were synthesized. 3'-Azido-3'-deoxy-6-azauridine, 4-deoxyuridine, 2-thiouridine, 3-deazauridine, nitropyridinone and isocytidine derivatives were also synthesized as the drug analogues to explore their biological properties. 14 final products are novel and well characterized, while all of the 31 final products were synthesized by the new strategy from the corresponding novel key intermediates. The two key intermediates can be utilized to make all kinds of novel nucleoside derivatives by glycosylating with various heterocyclic bases.
Key words： azido-nucleoside; L-nucleoside; D-nucleoside; synthesis; glycosylation
Ren Hang , Tao Jingchao , An Haoyun . Synthesis of 3'-Azido-D/L-nucleosides[J]. Chinese Journal of Organic Chemistry, 2018 , 38(1) : 138 -147 . DOI: 10.6023/cjoc201708005
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