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Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions.

ABSTRACT: A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.

SUBMITTER: Traverssi MG

PROVIDER: S-EPMC8695230 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions.

Traverssi Miqueas G MG Peñéñory Alicia B AB Varela Oscar O Colomer Juan P JP

RSC advances 20210301 16

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-<i>O</i>-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitu ...[more]

PMID: 35423421

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Dataset Information

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions.

Publications

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions.

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