A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.
A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.
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DOI：
10.1002/chem.201905576
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发表时间：
2020-06-26
期刊：
影响因子：
--
通讯作者：
Demchenko AV
中科院分区：
文献类型：
--
作者：
Geringer SA;Singh Y;Hoard DJ;Demchenko AV
继我们发现在催化TMSOTf或TfOH存在下，银(I)氧化物促进的糖基溴化物与糖基溴化物的糖基化反应可以大大加速之后，本文报道了一个新的发现，即在这些反应条件下，糖基氯化物是更有效的糖基供体。所开发的反应条件与多种糖基氯化物反应良好。苯甲酰化和苄基化的氯化物都成功地糖化了，这些反应条件对偶联含氮和硫原子的底物是有效的。这种糖基化的另一个方便的特点是，这个反应的进展可以用肉眼来监测，反应的完成可以通过Ag2O特征深色的消失来判断。
Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, reported herein is a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated chlorides were successfully glycosidated, and these reaction conditions were effective in coupling substrates containing nitrogen and sulfur atoms. Another convenient feature of this glycosylation is that the progress of this reaction can be monitored by eye, and the completion of the reaction can be judged by the disappearance of characteristic dark color of Ag2O.
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影响因子：
3.1
作者：
BYRAMOVA, NE;TUZIKOV, AB;BOVIN, NV
通讯作者：
BOVIN, NV
影响因子：
15
作者：
Garcia, BA;Gin, DY
通讯作者：
Gin, DY
影响因子：
16.6
作者：
Huang, XF;Huang, LJ;Ye, XS
通讯作者：
Ye, XS
影响因子：
3.2
作者：
Geringer, Scott A.;Demchenko, Alexei V.
通讯作者：
Demchenko, Alexei V.
影响因子：
4
作者：
Chiba, H;Funasaka, S;Mukaiyama, T
通讯作者：
Mukaiyama, T