ArticleChemical science2022
Recyclable fluorous-tag assisted two-directional oligosaccharide synthesis enabled by interrupted Pummerer reaction mediated glycosylation.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 15 citations in OpenAlex.
- Polytetrafluoroethylene-Assisted Rapid Preparation of α‑Oligomannosides Containing Mannose-6-Phosphate Residues.ACS omega · 2026Article
- Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition.Organic letters · 2025Article
- A Dual Role for theOrganic letters · 2024Article
- A fluorous-tag-assisted fluorescent probe for simple and selective detection of hydrogen sulfide: application for turbid dyeing solutions.RSC advances · 2023Article
- Kukhtin-Ramirez-Reaction-Inspired Deprotection of Sulfamidates for the Synthesis of Amino Sugars.Molecules (Basel, Switzerland) · 2022Article
- Diversity-Oriented Synthesis of a Molecular Library of Immunomodulatory α-Galactosylceramides with Fluorous-Tag-Assisted Purification and Evaluation of Their Bioactivities in Regard to IL-2 Secretion.International journal of molecular sciences · 2022Article
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Herein, we report a novel fluorous-tag assisted two-directional oligosaccharide assembly strategy, which maintained the high coupling efficiency of solution-phase synthesis and featured the advantage of an easy purification process comparable to solid-phase synthesis. A well-designed fluorous tag was decorated on the latent anomeric leaving group in interrupted Pummerer reaction mediated (IPRm) glycosylation. The high efficiency of the in-solution phase glycosylation and the unique affinity of the fluorous tag towards polytetrafluoroethylene (PTFE) particles allowed flexible assembly from the reducing end to the non-reducing end and 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 enabling the elongation of the carbohydrate chain from the non-reducing end to the reducing end as well as the recovery of the fluorous tag. The present two-directional synthetic strategy is used to assemble the repeating unit of
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.