Reactivity Tuning by Ring Size: A Glycosylation Protocol Using Thiophene-Scaffolded Glycosyl Donors
A thiophene-scaffolded alkyne-activating glycosyl donor has been developed, enabling fine reactivity control through ring-size modulation. The expanded spatial arrangement between the carbonyl and alkyne units confers distinct reactivity compared to the classical Yu's donor, facilitating efficient one-pot oligosaccharide assembly under single activation conditions. This reactivity differentiation also supports orthogonal, reactivity-based glycosylation strategies. The thiophene-based ATC donor is readily prepared, bench-stable, and broadly applicable, providing a practical and tunable platform for programmable glycosylation.
Authors
- Meifang Yang (ORCID: https://orcid.org/0000-0001-9899-3378)
- Yi-Yong Qiu (ORCID: https://orcid.org/0009-0009-2933-7786)
- Houchao Tao (ORCID: https://orcid.org/0000-0001-7598-0275)
- Jingyu Tian
- Shusheng Lai
- Xin Hua Zhou (ORCID: https://orcid.org/0000-0002-5580-7907)
- Liya Yang
- Ming Chen (ORCID: https://orcid.org/0000-0002-2045-0725)
- Mengyu Li (ORCID: https://orcid.org/0000-0001-5020-8676)
- Xiangwei Zheng (ORCID: https://orcid.org/0000-0001-5616-9284)
- Zijie Zhou (ORCID: https://orcid.org/0009-0001-4410-339X)
- Yan Tan (ORCID: https://orcid.org/0000-0003-0938-7996)
Institutions
- Guangxi University (CN)
- Shanghai University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-11
- DOI
- https://doi.org/10.1021/acs.orglett.5c04703
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00