An Efficient Approach to the Synthesis of Nucleosides: Gold(I)-Catalyzed N-Glycosylation of Pyrimidines and Purines with Glycosyl ortho-Alkynyl Benzoates

被引：144
|
作者：
Zhang, Qingju [1 ,2 ]
Sun, Jiansong [1 ]
Zhu, Yugen [1 ]
Zhang, Fuyi [2 ]
Yu, Biao [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Zhengzhou Univ, Dept Chem, Zhengzhou, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 21期
基金：
中国国家自然科学基金;
关键词：
glycosylation; gold; homogeneous catalysis; nucleosides; purines; ACID RELATED-COMPOUNDS; STEREOSELECTIVE-SYNTHESIS; MODIFIED OLIGONUCLEOTIDES; REGIOSELECTIVE SYNTHESIS; ORTHO-ALKYNYLBENZOATES; MITSUNOBU REACTIONS; D-RIBOFURANOSIDES; RIBOSYL DONORS; ANALOGS; 2-N-ACETYL-6-O-DIPHENYLCARBAMOYLGUANINE;
D O I：
10.1002/anie.201100514
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Persuaded with gold: The title reaction in the presence of [Ph 3PAuNTf2] (Tf=trifluoromethanesulfonyl) led conveniently to the corresponding nucleosides with excellent regioselectivity (see scheme). Even purine derivatives underwent this transformation owing to the mild conditions, which enabled the use of protecting groups that would not usually be compatible with N-glycosylation conditions. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：4933 / 4936
页数：4
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