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From d- to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation.

ABSTRACT: Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps.

SUBMITTER: Wan ICS

PROVIDER: S-EPMC6759743 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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From d- to l-Monosaccharide Derivatives via Photodecarboxylation-Alkylation.

Wan I C Steven ICS Witte Martin D MD Minnaard Adriaan J AJ

Organic letters 20190912 18

Photodecarboxylation-alkylation of conformationally locked monosaccharides leads to inversion of stereochemistry at C5. This allows the synthesis of l-sugars from their readily available d-counterparts. Via this strategy, methyl l-guloside was synthesized from methyl d-mannoside in 21% yield over six steps. ...[more]

PMID: 31512472

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