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Revisit of the phenol O-glycosylation with glycosyl imidates, BF3 center dot OEt2 is a better catalyst than TMSOTf
Alternative Title对糖基亚胺酯的酚糖苷化的重新审视: BF3?OEt2 是比TMSOTf更好的催化剂
Li YL(李亚莉); Mo HP(莫华萍); Lian GY(连高焱); Yu B(俞飚)
2012
Source PublicationCarbohydr. Res.
ISSN0008-6215
Volume363Pages:14-22
AbstractWith BF3 center dot OEt2 as the catalyst, the glycosylation of phenols with glycosyl trichloroacetimidates (or N-phenyl trifluoroacetimidates) bearing 2-O-participating groups leads to the desired 1,2-trans-O-glycosides in generally excellent yields without formation of the 1,2-cis-anomers. However, with TMSOTf as the catalyst, the outcomes of the corresponding phenol O-glycosylation are highly dependent on the nucleophilicity of the phenols; less nucleophilic is the phenol, higher amounts of the 1,2-cis-O-glycoside together with more side-products are generated. 1,2-Orthoesters have been found to be the major products at a low temperature (< -70 degrees C) in all these phenol O-glycosylation reactions, which are transformed into the final products at a higher temperature. BF3 center dot OEt2 is an effective catalyst to promote the conversion of 1,2-orthoesters into the corresponding 1,2-trans-O-glycosides. However, the 1,2-orthoesters could be converted into the dioxolenium triflate and glycosyl triflate in the presence of TMSOTf, these intermediates which might be in equilibrium with the glycosyl oxocarbenium related species lead to the final mixture of the alpha/beta-O-glycosides and side-products. (C) 2012 Elsevier Ltd. All rights reserved.
Subject Area生命有机化学
Department中科院上海有机化学研究所; 天津大学
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000310924600003
Citation statistics
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/28575
Collection生命有机化学国家重点实验室
Corresponding AuthorYu B(俞飚)
Recommended Citation
GB/T 7714
Li YL,Mo HP,Lian GY,et al. Revisit of the phenol O-glycosylation with glycosyl imidates, BF3 center dot OEt2 is a better catalyst than TMSOTf[J]. Carbohydr. Res.,2012,363:14-22.
APA 李亚莉,莫华萍,连高焱,&俞飚.(2012).Revisit of the phenol O-glycosylation with glycosyl imidates, BF3 center dot OEt2 is a better catalyst than TMSOTf.Carbohydr. Res.,363,14-22.
MLA 李亚莉,et al."Revisit of the phenol O-glycosylation with glycosyl imidates, BF3 center dot OEt2 is a better catalyst than TMSOTf".Carbohydr. Res. 363(2012):14-22.
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