Thiosugar nucleotide analogs: Synthesis of 5′-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-α-d-galactopyranosyl diphosphate) Original Research Article

The synthesis of a novel analog of uridine diphosphate galactose (UDP-Gal) is described. A sulfur atom was inserted into the 6-position of galactose to give uridine 5′-(2,3,4-tri-O-acetyl-6-S-acetyl-6-thio-α-d-galactopyranosyl diphosphate). This peracetylated thiol analogue of UDP-Gal has been synthesized in nine steps starting from methyl α-d-galactopyranoside in an overall yield of 3%.