Citation: Chai Yong-Hai, Feng Ying-Le, Wu Jing-Jing, Deng Chu-Qiao, Liu Ai-Yun, Zhang Qi. Recyclable benzyl-type fluorous tags: Preparation and application in oligosaccharide synthesis[J]. Chinese Chemical Letters, ;2017, 28(8): 1693-1700. doi: 10.1016/j.cclet.2017.06.020 shu

Recyclable benzyl-type fluorous tags: Preparation and application in oligosaccharide synthesis

Chai Yong-Hai ^a,b,*,, ,
Feng Ying-Le ^a,b ,
Wu Jing-Jing ^a,b ,
Deng Chu-Qiao ^a,b ,
Liu Ai-Yun ^a,b ,
Zhang Qi ^b,*,,

a.
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Shaanxi Normal University, Xi'an 710119, China
b.
School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China

Corresponding author: Chai Yong-Hai, ychai@snnu.edu.cn Zhang Qi, qiqizhang@snnu.edu.cn

Received Date: 8 May 2017
Revised Date: 29 May 2017
Accepted Date: 16 June 2017
Available Online: 19 August 2017

Figures(6)

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 tagtethered 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.
- Recyclable,
- Benzyl-type,
- Fluorous tag,
- Carbohydrates
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