Intramolecular Displacement Reactions Involving Sulfur Leading to the Formation of 3,6-Thiaanhydro Sugar Derivatives during the Synthesis of 3,5-Dithioglucofuranose

During a synthesis of 3,5-dithio-glucofuranose, we discovered two interesting intramolecular displacement reactions involving thiolate sulfur on the one hand and a thiirane sulfur on the other. Both generated 3,6-thiaanhydro structures. We solved the intramolecular displacement problem by using a 5-S,6-O-isopropylidene protecting group and accomplished 3,5-dithioglucofuranose synthesis in 9% overall yield.

Automated summary

In this study, two interesting intramolecular displacement reactions involving thiolate sulfur and thiirane sulfur were discovered during the synthesis of 3,5-dithio-glucofuranose. The use of a 5-S,6-O-isopropylidene protecting group successfully solved the intramolecular displacement problem, leading to the synthesis of 3,5-dithio-glucofuranose with a 9% overall yield.