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Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.

ABSTRACT: An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylmethyl and tert-butyldimethylsilyl ethers. The process affords the desired target compounds in 57-74% overall yield in just 21-37 minutes of flow time. Furthermore, unlike batch conditions, the flow processes avoided the need for active cooling to prevent unwanted exotherms and required shorter reaction times.

SUBMITTER: Yalamanchili S

PROVIDER: S-EPMC7289173 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.

Yalamanchili Subbarao S Nguyen Tu-Anh V TV Pohl Nicola L B NLB Bennett Clay S CS

Organic & biomolecular chemistry 20200501 17

An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylmethyl and tert-butyldimethylsilyl ethers. The process affords the desired target compounds in 57-74% overall yield in just 21-37 minutes of flow time. Furthermore, unlike batch conditions, the flow processes avoided the need for active cooling to ...[more]

PMID: 32293636

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