Recyclable Fluorous-Tag Assisted Two-Directional Oligosaccharide Synthesis Enabled by Interrupted Pummerer Reaction Mediated Glycosylation

Abstract

Herein, we report a novel fluorous-tag assisted two-directional oligosaccharide assembly strategy, which combines the advantages of solution-phase synthesis and solid-phase synthesis. A well-designed fluorous-tag was decorated on the latent anomeric leaving group in interrupted Pummerer reaction mediated (IPRm) glycosylation. High efficiency of the in-solution phase glycosylation and unique affinity of the fluorous-tag towards polytetrafluoroethylene (PTFE) particles allowed flexible assembly from reducing end to non-reducing end and the fast purification by PTFE-assisted filtration. Moreover, the fluorous-tagged latent anomeric leaving group could be activated by oxidation and cleaved by IPRm glycosylation thus enabled the elongation of carbohydrate chain from non-reducing end to reducing end as well as the recovery of fluorous-tag. The present two-directional synthetic strategy is used to assemble the repeating unit of Streptococcus pneumoniae type 14 capsular polysaccharide

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Mar 2022
Accepted
21 Jun 2022
First published
22 Jun 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022, Accepted Manuscript

Recyclable Fluorous-Tag Assisted Two-Directional Oligosaccharide Synthesis Enabled by Interrupted Pummerer Reaction Mediated Glycosylation

L. Cai, Q. Chen, J. Guo, Z. Liang, D. Fu, L. Meng, J. Zeng and Q. Wan, Chem. Sci., 2022, Accepted Manuscript , DOI: 10.1039/D2SC01700H

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