Gold-Catalyzed Synthesis of 2-Deoxy Glycosides Using S-But-3-ynyl Thioglycoside Donors

Gold-Catalyzed Synthesis of 2-Deoxy Glycosides Using S-But-3-ynyl Thioglycoside Donors
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DOI:
10.1021/cs300670k
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发表时间:
2013-01-01
期刊:
影响因子:
12.9
通讯作者:
Zhu, Jianglong
Zhu, Jianglong
中科院分区:
化学1区
文献类型:
--
作者:
Adhikari, Surya;Baryal, Kedar N.;Zhu, Jianglong

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描述了一种温和且原子经济的金 (I) 催化糖基化,用于使用工作台稳定的 2-脱氧 S-But-3-ynyl 硫代糖苷供体立体选择性合成 2-脱氧 α-糖苷。在最佳条件下,2-脱氧和2,6-二脱氧硫代糖苷供体能够与各种伯醇、仲醇和叔醇受体反应,以良好至优异的产率提供α-选择性糖苷。
A mild and atom-economic gold(I)-catalyzed glycosylation for stereoselective synthesis of 2-deoxy alpha-glycosides using bench-stable 2-deoxy S-But-3-ynyl thioglycoside donors has been described. Under optimal conditions, 2-deoxy and 2,6-dideoxy thioglycoside donors were able to react with a variety of primary, secondary, and tertiary alcohol acceptors to afford alpha-selective glycosides in good to excellent yields.