Synthesis of 5-Thio-D- Galactopyranose

Abstract

5-Thio-D-galactopyranose has been synthesized from diacetone galactofuranose in nine steps and 13.4% overall yield. The key step involved a successful conversion of furanosyl 5,6-epoxide with an L-altrose configuration into the corresponding 5,6-thiirane D-galactose derivative, which was hydrolyzed to the target compound.

Keywords:

• 5-Thio-D-galactopyranose
• Glycosidase inhibitors
• Thiirane
• Galactofuranose
• Thiosugars

ACKNOWLEDGMENTS

This work was supported in partial by the National Basic Research Program of China (Grant 2012CB822101), National Innovative Drug Foundation (Project 2012ZX09502001), and NNSF of China (Project 21072217). The authors also thank Prof. Jianjun Zhang for providing diacetone D-galactofuranose (synthesized in the Key Technologies R&D Program of China, 2012BAK25B03, CAU) as the starting material.