文献类型：期刊文献

英文题名：Synthesis of Nucleosides and Deoxynucleosides via Gold(I)- Catalyzed N-Glycosylation of Glycosyl (Z)-Ynenoates

作者：Liu, Rongkun[1];Chen, Yan[1];Zheng, Jibin[1];Zhang, Lvfeng[1];Xu, Tong[1];Xu, Peng[2];Yang, You[1]

机构：[1]East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Met, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm,Shanghai Key Lab New Drug Design,Minist, Shanghai 200237, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

年份：2022

卷号：24

期号：51

起止页码：9479

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000901561000001)】；

基金：ACKNOWLEDGMENTS Financial support from the National Natural Science Foundation of China (21871081, 22071054) , the Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission) , the First-Class Discipline Construction and Characteristic Devel-opment Guidance Funds for the Central Universities (SLC13223002) , and the Shanghai Key Laboratory of New Drug Design (SKLNDD-KF-202202) is gratefully acknowl-edged.

语种：英文

摘要：Nucleoside analogues are widely used as anticancer and antiviral drugs. Here, we develop a highly efficient gold(I)-catalyzed N-glycosylation approach for versatile synthesis of various types of nucleosides and deoxynucleosides with glycosyl (Z)-ynenoates as donors. The wide scope of the N-glycosylation approach was demonstrated by the synthesis of 31 pyrimidine nucleosides and 8 purine nucleosides. Remarkably, the gold(I)-catalyzed N-glycosylation of pyranosyl (Z)-ynenoates with purines was found to be very effective for regioselective synthesis of pyranosyl N9 purine nucleosides. Based on the catalytic N-glycosylation approach, convenient synthesis of two 5 '-deoxynucleosides drugs (capecitabine and galocitabine), four 2 '-deoxynucleoside drugs (floxuridine, trifluridine, decitabine and cladribine), four 3 ',5 '- dideoxynucleoside analogues, and four 2 ',5 '-dideoxynucleoside analogues was achieved in a collective manner.