Collect. Czech. Chem. Commun. 1981, 46, 2197-2202

Synthesis of nucleoside analogs by addition-cyclization reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate

Marián Valentínya, Augustin Martvoňb and Pavol Kováčc

a Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava
b Institute for Drug Research, 801 00 Bratislava
c Institute of Chemistry, Slovak Academy of Sciences, 809 33 Bratislava


Reactions of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (I) with various hydrazides gave 4-substituted 1-acylthiosemicarbazides. Their cyclization, by treatment with sodium methoxide, gave analogs of nucleosides. The reaction of (I with thioglycolic acid to give substituted 1,3-thiadiazolidine has also been studied.