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Updated: May 24, 2026
13:36
Generation of Monocyte-Derived Dendritic Cells with Differing Sialylated Phenotypes
Published on: October 20, 2023
Stereoselective, electrophilic α-C-sialidation.
Amandine Noel1, Bernard Delpech, David Crich
1Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
Organic Letters
|February 17, 2012
Summary
Researchers developed a new method for synthesizing sialyl C-glycosides using protected sialyl phosphates. This approach offers high yield and selectivity, minimizing unwanted byproducts and preserving key functional groups.
Area of Science:
- Carbohydrate Chemistry
- Organic Synthesis
- Glycoscience
Background:
- Sialyl C-glycosides are important in biological systems.
- Previous synthetic methods often lack efficiency or selectivity.
- Protecting group strategies are crucial for complex carbohydrate synthesis.
Purpose of the Study:
- To develop a novel and efficient method for synthesizing alpha-sialyl C-glycosides.
- To investigate the utility of oxazolidinone-protected sialyl phosphates in C-glycosylation reactions.
- To establish a mild deprotection strategy that preserves the acetamide group.
Main Methods:
- Reaction of oxazolidinone-protected alpha- and beta-sialyl phosphates with allyltributylstannane.
- Utilizing trimethylsilyl enol ethers as coupling partners.
- Mild cleavage of the oxazolidinone protecting group.
Main Results:
- High yields and excellent stereoselectivity were achieved for alpha-sialyl C-glycosides.
- The oxazolidinone ring effectively suppressed elimination to form glycals.
- The acetamide group remained intact after mild deprotection.
Conclusions:
- Oxazolidinone protection is a valuable strategy for the synthesis of sialyl C-glycosides.
- The developed method provides a robust route to complex sialylated structures.
- This approach facilitates access to biologically relevant sialyl C-glycosides.
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