Recyclable benzyl-type fluorous tags: Preparation and application in oligosaccharide synthesis
Recyclable benzyl-type fluorous tags: Preparation and application in oligosaccharide synthesis
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可回收的苄基型氟标签的制备及其在寡糖合成中的应用
DOI：
10.1016/j.cclet.2017.06.020
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发表时间：
2017-08-01
影响因子：
9.1
通讯作者：
Zhang, Qi
中科院分区：
文献类型：
--
作者：
Chai, Yong-Hai;Feng, Ying-Le;Zhang, Qi
We herein described the design, synthesis and application of two recyclable benzyl-type fluorous tags with double fluorous chains. The benzyl-type fluorous tags were prepared in 3 steps from a commercially available fluorous alcohol. The glycosylation of the benzyl-type tags with imidate donors proceeded smoothly to provide the corresponding fluorous-tagged carbohydrates in good to excellent yields, which were readily purified by fluorous solid-phase extraction (FSPE). Efficient removal of the tags from tag tethered carbohydrates were conducted under the common catalytic hydrogenation condition and the initial benzyl-type fluorous tags could be regenerated via a 2-step simple procedure in 69%-93% yields. The utility of the new benzyl-fluorous tag was demonstrated via the FSPE-assisted synthesis of oligosaccharides Gb3. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
