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

Jan Choutka; Radek Pohl; Kamil Parkan

doi:10.1021/acsomega.8b00901

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

ACS Omega. 2018 Jul 16;3(7):7875-7887. doi: 10.1021/acsomega.8b00901. eCollection 2018 Jul 31.

Authors

Jan Choutka¹, Radek Pohl², Kamil Parkan¹

Affiliations

¹ Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Prague, Technická 5, 166 28 Prague, Czech Republic.
² Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 166 10 Prague, Czech Republic.

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 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.