Synthesis of 2,3-dideoxy-C-3-thiopyrimidine based new Glycohybrids

The stereoselective synthesis of C-3-thiopyrimidine-based glycohybrids remains largely under explored. An efficient and highly stereoselective one-pot organocatalytic strategy has been developed for the synthesis of new 2,3-dideoxy-C-3-thiopyrimidine-based C-3-thio-glycohybrids from Perlin's aldehydes and pyrimidine-2-thione derivatives under mild, metal-free conditions. l-proline used as an inexpensive organocatalyst, the reaction proceeds smoothly at room temperature to afford twenty new glycohybrids in good to very good yields with excellent equatorial selectivity at C-3. The structures and stereochemical configurations of the products were established by spectroscopic analyses and single-crystal X-ray diffraction studies. The operational simplicity, metal-free nature, and high stereoselectivity make this protocol an attractive and sustainable approach for accessing privileged C-3-thioglycohybrids.