MOP and EE Protecting Groups in Synthesis of alpha- or beta-Naphthyl-C-Glycosides from Glycals

0492083 - ÚOCHB 2019 RIV US eng J - Journal Article
Choutka, J. - Pohl, Radek - Parkan, K.
MOP and EE Protecting Groups in Synthesis of alpha- or beta-Naphthyl-C-Glycosides from Glycals.
ACS Omega. Roč. 3, č. 7 (2018), s. 7875-7887. ISSN 2470-1343. E-ISSN 2470-1343
Institutional support: RVO:61388963
Keywords : d-galactopyranoside * coupling reaction * vinyl ethers
OECD category: Organic chemistry
Impact factor: 2.584, year: 2018
https://pubs.acs.org/doi/10.1021/acsomega.8b00901

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 alpha- or beta-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.
Permanent Link: http://hdl.handle.net/11104/0285952