Simple synthesis of glycosylthiols and thioglycosides by rearrangement of O-glycosyl thionocarbamates

R Komor; A Kasprzycka; G Pastuch-Gawołek; W Szeja

doi:10.1016/j.carres.2014.07.001

Simple synthesis of glycosylthiols and thioglycosides by rearrangement of O-glycosyl thionocarbamates

Carbohydr Res. 2014 Sep 19:396:37-42. doi: 10.1016/j.carres.2014.07.001. Epub 2014 Jul 9.

Authors

R Komor¹, A Kasprzycka², G Pastuch-Gawołek², W Szeja²

Affiliations

¹ Silesian University of Technology, Faculty of Chemistry, Chair of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland. Electronic address: rkomor@polsl.pl.
² Silesian University of Technology, Faculty of Chemistry, Chair of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.

PMID: 25079597
DOI: 10.1016/j.carres.2014.07.001

Abstract

The synthesis of thioglycosides has been achieved in a high yielding process employing thionocarbamates prepared from protected reducing sugars and N-alkyl isothiocyanate in the presence of a non-nucleophilic base (K2CO3). In the key step of the synthesis, thionocarbamates were treated with Lewis acid (TMSOTf) to give O,S-rearrangement products that were applied to the synthesis of both anomers of heteroaryl thioglycosides.

Keywords: Glycopyranosyl thionocarbamates; O,S-rearrangement; Thioglycosides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbamates / chemistry*
Glycosylation
Isothiocyanates / chemistry
Sulfhydryl Compounds / chemical synthesis*
Thioglycosides / chemical synthesis*

Substances

Carbamates
Isothiocyanates
Sulfhydryl Compounds
Thioglycosides
isothiocyanic acid