Abstract
Application of the Helferich method to the preparation of thioglycosides was performed in dichloroethane at room temperature by use of SnCl4 as catalyst. The reaction gave 1-thio-β-D-glucopyranoside from penta-O-acetyl-β-D-glucopyranose and thiophenol in good yield. However, the similar reaction with methyl 1, 2, 3, 4-tetra-O-acetyl-β-D-glucopyranuronate and thiophenol gave an unpredicted product, 3, 4-di-O-acetyl-6-methoxy 6-thiophenyl-α-D-glucopyranose 1, 2-(phenylthio orthoacetate). The structure was confirmed by analytical and spectral data.
