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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 | 2018-01-01

REPOSITORIES: biostudies

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