Solvent-Free Preparation of Glycosyl Isothiocyanates

Thisbe K. Lindhorst; Christoffer Kieburg

doi:10.1055/s-1995-4086

Synthesis 1995; 1995(10): 1228-1230
DOI: 10.1055/s-1995-4086

short paper

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Solvent-Free Preparation of Glycosyl Isothiocyanates

Thisbe K. Lindhorst^* , Christoffer Kieburg

^*Institut für Organische Chemie der Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany, Fax +49(40)41234325; E-mail tklind@chemie.uni-hamburg.de

Abstract

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By a novel solvent-free procedure, peracetylated glycosyl bromides are reacted with potassium thiocyanate in the melt to give the corresponding glycosyl isothiocyanates. The method is applicable to several glycosyl bromides tested, including classical hexoses and pentoses, deoxy sugars and even disaccharides. No glycosyl thiocyanates are obtained. In general, the glycosyl isothiocyanates are formed stereoselectively having 1,2-trans configuration in yields between 41-74%.

carbohydrate synthesis melting procedure glycosyl isothiocyanates disaccharide isothiocyanates glycosyl bromides

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