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MOP and EE Protecting Groups in Synthesis of ?- or ?-Naphthyl-C-Glycosides from Glycals.

ABSTRACT: The development of effective protection strategies is essential in the synthesis of complex carbohydrates and glycomimetics. This article describes a versatile four-stage protocol for the synthesis of ?- or ?-aryl-C-glycosides from unprotected d-glycals using two acetal protecting groups, ethoxyethyl and methoxypropyl, which are stable under harsh basic conditions and convenient for the C-1 metalation of glycals. Their stability was investigated in subsequent cross-coupling reactions with 1-iodonaphthalene followed by oxidative/reductive transformations to naphthyl-C-glycosides.

SUBMITTER: Choutka J

PROVIDER: S-EPMC6644498 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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MOP and EE Protecting Groups in Synthesis of α- or β-Naphthyl-C-Glycosides from Glycals.

Choutka Jan J Pohl Radek R Parkan Kamil K

ACS omega 20180716 7

The development of effective protection strategies is essential in the synthesis of complex carbohydrates and glycomimetics. This article describes a versatile four-stage protocol for the synthesis of α- or β-aryl-C-glycosides from unprotected d-glycals using two acetal protecting groups, ethoxyethyl and methoxypropyl, which are stable under harsh basic conditions and convenient for the C-1 metalation of glycals. Their stability was investigated in subsequent cross-coupling reactions with ...[more]

PMID: 31458930

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