Alkenyl Glycosyl Donors as Versatile Tools for Carbohydrate Synthesis
Zhiwen Liao1, Jing Zeng1, Lingkui Meng1
1School of Pharmacy, Huazhong University of Science and Technology, Wuhan, Hubei, 430030, China.
Chemistry, an Asian Journal
|October 29, 2025
Summary
Alkenyl glycosyl donors, like n-pentenyl glycosides, offer versatile reactivity for synthesizing complex carbohydrates. Their diverse activation methods and compatibility with advanced strategies significantly advance glycoscience.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
Background:
- Alkenyl glycosyl donors feature alkenyl leaving groups at the anomeric position.
- Initial development focused on n-pentenyl glycosides (NPGs) and n-pentenyl esters (NPEs).
Purpose of the Study:
- To review the development and applications of alkenyl glycosyl donors.
- To highlight their versatile reactivity and synthetic utility.
Main Methods:
- Exploration of diverse alkenyl donor types (ether, ester, orthoester, thioether, sulfone).
- Investigation of various activation mechanisms (halogen-mediated, acid-promoted, photoredox).
- Assessment of compatibility with modern synthetic strategies (armed/disarmed, orthogonal, automated glycan assembly).
Main Results:
- Demonstration of versatile reactivity across various alkenyl glycosyl donor classes.
- Successful activation through multiple pathways, enabling broad applicability.
- Significant advancements in the synthesis of complex carbohydrates facilitated by these donors.
Conclusions:
- Alkenyl glycosyl donors are powerful tools in modern carbohydrate synthesis.
- Their adaptable nature and compatibility with advanced methods drive innovation in glycoscience.
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