Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides
文献类型：期刊论文
| 作者 | Kong, Fanzuo |
| 刊名 | CARBOHYDRATE RESEARCH
 |
| 出版日期 | 2007-02-26 |
| 卷号 | 342期号:1页码:345-373 |
| 关键词 | Orthoester Rearrangement Oligosaccharide Synthesis |
| 英文摘要 | Formation of sugar-sugar orthoesters consisting of a fully acylated mono- or disaccharide donor and a partially protected mono- or disaccharide acceptor is regioselective, and rearrangement of the orthoesters via RO-(orthoester)C bond cleavage gives a dioxolenium ion intermediate leading to 1,2-trans glycosidic linkage. The activity order of hydroxyl groups in the partially protected mannose and glucose acceptors is 6-OH > 3-OH > 2- or 4-OH. The coupling reactions with acylated glycosyl trichloroacetimidates as the donors usually give orthoesters as the intermediates specially when the coupling is carried out at slowed rates, and this is successfully used in regio- and stereoselective syntheses of oligosaccharides. Mannose and rhamnose orthoesters readily undergo O-2-(orthoester)C bond breaking, and this is used for synthesis of alpha-(1 -> 2)-linked oligosaccharides. (1 -> 3)-Glucosylation is special since the rearrangement of its sugar orthoester intermediates can occur with either RO-(orthoester)C bond cleavage with formation of the dioxolenium ion leading to 1,2-trans linkage, or C-1-O-1 bond cleavage leading to 1,2-cis linkage, and this is dependent upon the structures of donor and acceptor that compose the orthoester. (c) 2006 Elsevier Ltd. All rights reserved. |
| WOS记录号 | WOS:000244548700004 |
| 源URL | [http://ir.rcees.ac.cn/handle/311016/22671]  |
| 专题 | 生态环境研究中心_中国科学院环境生物技术重点实验室 |
| 推荐引用方式 GB/T 7714 | Kong, Fanzuo. Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides[J]. CARBOHYDRATE RESEARCH,2007,342(1):345-373. |
| APA | Kong, Fanzuo.(2007).Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides.CARBOHYDRATE RESEARCH,342(1),345-373. |
| MLA | Kong, Fanzuo."Recent studies on reaction pathways and applications of sugar orthoesters in synthesis of oligosaccharides".CARBOHYDRATE RESEARCH 342.1(2007):345-373. |
入库方式： OAI收割
来源：生态环境研究中心
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