Investigation of the Reactivities of Halogen-Substituted Bicyclic Sialic Acid Donors and Their Application
We previously developed a fully stereoselective α-sialylation using a macrobicyclic donor. We report that dihalogen substitutions on the macrocyclic moiety greatly enhance the reactivity of macrobicyclic donors. Furthermore, by using Cl- and F-substituted donors, we achieved late-stage regioselective C5 modifications of α(2,8)-linked disialic acids─highly challenging synthetic targets of significant biological importance. This study broadens the utility of the fully stereoselective α-sialylation and underscores the importance of amino group modifications in glycosylation.
Authors
- Sung-Chi Lin
- Hidenori Tanaka (ORCID: https://orcid.org/0000-0001-5307-4909)
- Hiromune Ando (ORCID: https://orcid.org/0000-0002-0551-0830)
- Naoko Komura (ORCID: https://orcid.org/0000-0002-8104-750X)
- Cheng‐Chung Wang (ORCID: https://orcid.org/0000-0002-2562-0658)
- Taro Udagawa (ORCID: https://orcid.org/0000-0002-4072-253X)
- Akihiro Imamura (ORCID: https://orcid.org/0000-0002-7860-992X)
- Nobuhiko Nishio (ORCID: https://orcid.org/0000-0002-8726-5022)
- Hideharu Ishida (ORCID: https://orcid.org/0000-0002-8625-0929)
- Maina Takahashi
- Sakuma Yasutake
Institutions
- Institute of Chemistry, Academia Sinica (TW)
- Gifu University (JP)
- Academia Sinica (TW)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-22
- DOI
- https://doi.org/10.1021/acs.orglett.5c03369
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00