Highly Stereoselective α-Glycosylation by Acid–Base Catalysis with the Help of Two Additives: The Counterion of the Acid and a Heterocyclic Base
Abstract The stereoselective synthesis of 1,2-cis glycosides remains a longstanding challenge in carbohydrate chemistry. Herein, we report a cooperative acid–base catalysis strategy based on N-iodosuccinimide/triethylsilane and 8-nitroquinoline for highly α-selective glycosylation with O-glycosyl trichloroacetimidate donors. This catalytic system enables the synthesis of over 50 glycosides in good to excellent yields under mild conditions. The synthetic utility was further demonstrated through gram-scale reactions and the convergent synthesis of an α-(1→6)-linked hexasaccharide.
Authors
- Richard R. Schmidt (ORCID: https://orcid.org/0000-0001-6398-9053)
- Hui Xiao (ORCID: https://orcid.org/0000-0001-5654-3846)
- Yuxin Han (ORCID: https://orcid.org/0009-0008-3978-3037)
- Tianlu Li (ORCID: https://orcid.org/0000-0002-0674-3687)
- Peng Peng (ORCID: https://orcid.org/0000-0003-4625-6610)
- Zhentao Zhang
- Qingling Cheng
- Tong Li
- Qin Li
- Hengjie Hu
Institutions
- Tianjin University of Commerce (CN)
- King University (US)
- Shandong University (CN)
- University of Konstanz (DE)
- Peking University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-09-08
- DOI
- https://doi.org/10.1021/acs.orglett.6c03526
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Shandong Province
- Key Technology Research and Development Program of Shandong
- National Key Research and Development Program of China