Defining the Scope of the Acid-Catalyzed Glycosidation of Glycosyl Bromides.
Defining the Scope of the Acid-Catalyzed Glycosidation of Glycosyl Bromides.
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DOI：
10.1002/chem.201904185
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发表时间：
2020-01-22
期刊：
影响因子：
--
通讯作者：
Demchenko AV
中科院分区：
文献类型：
--
作者：
Singh Y;Demchenko AV
最近发现，在催化 TMSOTf 的存在下，传统的氧化银 (I) 促进的糖基溴化（Koenigs-Knorr 反应）可以大大加速，本文报道了对该反应所有主要方面的专门研究。对多种银盐的彻底研究和对反应条件的仔细改进提高了对机理的理解。这反过来又导致这些糖基化所需的银盐量显着减少。该反应的进展可以用肉眼监测，通过Ag2O特征深色的消失来判断反应的完成。已获得更多证据表明苯甲酰化α-溴化物与其苯甲酰化对应物相比具有更高的反应性。
Following the recent discovery that traditional silver(I) oxide-promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic TMSOTf, reported herein is a dedicated study of all major aspects of this reaction. A thorough investigation of numerous silver salts and careful refinement of the reaction conditions led to an improved mechanistic understanding. This, in turn, led to a significant reduction in the amount of silver salt required for these glycosylations. The progress of this reaction can be monitored by naked eye, and the completion of the reaction can be judged by the disappearance of characteristic dark color of Ag2O. Further evidence on higher reactivity of benzoylated a-bromides in comparison to that of their benzylated counterparts has been acquired.
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DOI：
10.3891/acta.chem.scand.37b-0775
发表时间：
1983-01-01
期刊：
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY
影响因子：
--
作者：
BOCK, K;MELDAL, M
通讯作者：
MELDAL, M
影响因子：
--
作者：
Helferich, B;Bohn, E;Winkler, S
通讯作者：
Winkler, S
影响因子：
15
作者：
Garcia, BA;Gin, DY
通讯作者：
Gin, DY
影响因子：
3.1
作者：
Hunsen, M;Long, DA;Smith, AL
通讯作者：
Smith, AL
影响因子：
1.8
作者：
Agnihotri, Geetanjali;Misra, Anup Kumar
通讯作者：
Misra, Anup Kumar