中国科学院上海有机化学研究所机构知识库
Advanced  
SIOC OpenIR  > 生命有机化学国家重点实验室  > 期刊论文
学科主题: 生命有机化学
题名: Revisit of the phenol O-glycosylation with glycosyl imidates, BF3 center dot OEt2 is a better catalyst than TMSOTf
其他题名: 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
作者: Li YL(李亚莉) ; Mo HP(莫华萍) ; Lian GY(连高焱) ; Yu B(俞飚)
通讯作者: 俞飚
刊名: Carbohydr. Res.
发表日期: 2012
卷: 363, 页:14-22
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 天津大学
英文摘要: With 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.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000310924600003
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/28575
Appears in Collections:生命有机化学国家重点实验室_期刊论文

Files in This Item: Download All
File Name/ File Size Content Type Version Access License
2012547.pdf(1194KB)----开放获取--View Download

Recommended Citation:
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.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Google Scholar
Similar articles in Google Scholar
[李亚莉]'s Articles
[莫华萍]'s Articles
[连高焱]'s Articles
CSDL cross search
Similar articles in CSDL Cross Search
[李亚莉]‘s Articles
[莫华萍]‘s Articles
[连高焱]‘s Articles
Related Copyright Policies
Null
Social Bookmarking
Add to CiteULike Add to Connotea Add to Del.icio.us Add to Digg Add to Reddit
文件名: 2012547.pdf
格式: Adobe PDF
此文件暂不支持浏览
所有评论 (0)
暂无评论
 
评注功能仅针对注册用户开放,请您登录
您对该条目有什么异议,请填写以下表单,管理员会尽快联系您。
内 容:
Email:  *
单位:
验证码:   刷新
您在IR的使用过程中有什么好的想法或者建议可以反馈给我们。
标 题:
 *
内 容:
Email:  *
验证码:   刷新

Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.

 

 

Valid XHTML 1.0!
Powered by CSpace