Synthesis of sialyl halides with various acyl protective groups

Area of Science:

• Carbohydrate Chemistry
• Organic Synthesis

Background:

• Glycosyl halides are foundational glycosyl donors in glycosylation reactions.
• Recent advancements have improved their activation and oligosaccharide synthesis applications.
• Existing sialyl halides lack diversity, limiting sialoside synthesis.

Purpose of the Study:

• To synthesize novel sialyl chlorides and bromides with diverse protecting groups.
• To expand the range of available building blocks for sialoside synthesis.

Main Methods:

• Synthesis of six new N-acetyl- and N-trifluoroacetyl-sialyl chlorides and bromides.
• Utilized O-chloroacetyl and O-trifluoroacetyl protecting groups.
• Developed a new synthesis for N-trifluoroacetyl protected sialic acid methyl ester pentaol.

Main Results:

• Successfully synthesized six novel sialyl halide derivatives.
• Introduced new N-acetyl and N-trifluoroacetyl protected sialyl chlorides and bromides.
• Demonstrated the utility of O-chloroacetyl and O-trifluoroacetyl groups in sialyl halide synthesis.

Conclusions:

• The developed methods provide access to a broader range of sialyl halides.
• These new compounds enhance possibilities for synthesizing complex sialosides.
• The study contributes valuable new reagents to the field of carbohydrate chemistry.