title: Simple synthesis of glycosylthiols and thioglycosides by rearrangement of O-glycosyl thionocarbamates.
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.
authors: 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.
authors: R
authors: R
authors: Komor
authors: Silesian University of Technology, Faculty of Chemistry, Chair of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.
authors: A
authors: A
authors: Kasprzycka
authors: Silesian University of Technology, Faculty of Chemistry, Chair of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.
authors: G
authors: G
authors: Pastuch-Gawołek
authors: Silesian University of Technology, Faculty of Chemistry, Chair of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.
authors: W
authors: W
authors: Szeja
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D006031:Glycosylation; D017879:Isothiocyanates / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis*; D013865:Thioglycosides / Q000138:chemical synthesis*
chemical_list: D002219:Carbamates; D017879:Isothiocyanates; D013438:Sulfhydryl Compounds; D013865:Thioglycosides; C037152:isothiocyanic acid
keywords: Glycopyranosyl thionocarbamates; O,S-rearrangement; Thioglycosides