Synthesis of 4-thio- dD-mannose

Abstract

1,6-Anhydro-4- S-benzoyl-4-thio-β- D-mannopyranose, obtained by treatment of 1,6:3,4-dianhydro-β- D-talopyranose with pyridinium thiolbenzoate in N, N-di-methylformamide, was converted into its 2,3-di- O-acetyl derivative, which was acetolyzed to give 1,2,3,6-tetra- O-acetyl-4- S-benzoyl-4-thio- D-mannopyranose. Deacylation of the last-named compound with sodium methoxide in methanol gave syrupy 4-thio- D-mannose, which was characterized as 1,2,3,5,6-penta- O-acetyl-4-thio-α- and -β- D-mannofuranose.