Adaptation of Zemplén's conditions for a simple and highly selective approach to methyl 1,2-trans glycosides

Serena Traboni; Emiliano Bedini; Domenica Capasso; Fabiana Esposito; Alfonso Iadonisi

doi:10.1016/j.carres.2023.108824

Adaptation of Zemplén's conditions for a simple and highly selective approach to methyl 1,2-trans glycosides

Carbohydr Res. 2023 Jun:528:108824. doi: 10.1016/j.carres.2023.108824. Epub 2023 Apr 30.

Authors

Serena Traboni¹, Emiliano Bedini¹, Domenica Capasso², Fabiana Esposito¹, Alfonso Iadonisi³

Affiliations

¹ Department of Chemical Sciences, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy.
² Center for Life Sciences and Technologies (CESTEV), University of Naples Federico II, 80145, Naples, Italy.
³ Department of Chemical Sciences, University of Naples Federico II, Via Cinthia 4, 80126, Naples, Italy. Electronic address: iadonisi@unina.it.

PMID: 37141732
DOI: 10.1016/j.carres.2023.108824

Abstract

1,2-trans methyl glycosides can be readily obtained from peracetylated sugars through their initial conversion into glycosyl iodide donors and subsequent exposure of these latter to a slight excess of sodium methoxide in methanol. Under these conditions a varied set of mono- and disaccharide precursors afforded the corresponding 1,2-trans glycosides with concomitant de-O-acetylation in satisfying yields (in the range 59-81%). A similar approach also proved effective when using GlcNAc glycosyl chloride as the donor.

Keywords: 1,2-Trans glycosylations; Methyl glycosides; Zemplén's deacetylation.

MeSH terms

Acetylation
Carbohydrate Conformation
Disaccharides*
Glycosides*

Substances

Glycosides
Disaccharides