Studies on Nucleosides and Nucleotides. II. Synthesis of Glycosyl-2-thiothymines from Glycosylthioureas.

Abstract

Synthesis of glycosyl-2-thiothymine from glycosylthiourea was carried out. Acetylation of 1-β-D-glucopyranosylthiourea with acetic anhydride, glacial acetic acid, and perchloric acid was found to give 1-(tetra-O-acetyl-β-D-glucosyl) thiourea and it was condensed with 2-methyl-3-methoxyacryloyl chloride. Cyclization of its product afforded 1-β-D-glucopyranosyl-2-thiothymine. In a similar manner, thiourea, prepared from tri-O-benzoyl-D-ribofuranosyl chloride through isothiocyanate, afforded 1-β-D-ribofuranosyl-2-thiothymine by the same method. The structure of all the compounds synthesized was established.