Sonogashira cross-coupling as a key step in the synthesis of new glycoporphyrins

Glycoporphyrins are an important subclass of the porphyrin family of compounds. They have been intensively studied because of their biological importance, i.e. they exhibit increased solubility in polar solvents and they might provide better selectivity towards biological targets. New methods for th...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (9), p.2396-2404
Main Authors: Godlewski, Bartosz, Baran, Dariusz, de Robichon, Morgane, Ferry, Angélique, Ostrowski, Stanisław, Malinowski, Maciej
Format: Article
Language:English
Subjects:
Carbohydrates
Chemical Sciences
Cross coupling
Organic chemistry
Porphyrins
Selectivity
Synthesis
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Summary:Glycoporphyrins are an important subclass of the porphyrin family of compounds. They have been intensively studied because of their biological importance, i.e. they exhibit increased solubility in polar solvents and they might provide better selectivity towards biological targets. New methods for the efficient synthesis of these compounds are highly desired. Unfortunately, in most of the described methodologies, carbohydrate-linked porphyrins are obtained through hydrolyzable connections. Herein, the original route to new C–C conjugated glycoporphyrins via the Sonogashira cross-coupling is presented. The optimal conditions have been established and the most convenient synthetic strategy has been determined.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo01909k