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Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction.

ABSTRACT: A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and convenient sequence of reactions.

SUBMITTER: Serpico L

PROVIDER: S-EPMC8123786 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction.

Serpico Luigia L De Nisco Mauro M Cermola Flavio F Manfra Michele M Pedatella Silvana S

Molecules (Basel, Switzerland) 20210427 9

A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and c ...[more]

PMID: 33925409

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