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

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 1-iodonaphthalene followed by oxidative/reductive transformations to naphthyl-C-glycosides.