4-Thiopyranoside and 4-thiofuranoside derivatives of D-galactosamine

Article abstract of DOI:10.1016/S0008-6215(97)00218-8

Methyl 2-benzamido-2-deoxy-4-thio-α-D-galactopyranoside (7) was prepared in different ways starting from methyl 2-benzamido-3,6-di-O-benzoyl- 2-deoxy-α-D-glucopyranoside (1). A 4,6-epidithiogalactopyranoside was obtained from the 4-O-mesyl derivative of 1. The transformations of 7 into 2- benzamido-2-deoxy-4-thio-D-galactofuranose and into the corresponding methyl α- and β-4-thio-D-galactofuranosides are reported. The ²T₃ conformation is proposed for the α anomers of the prepared furanoid compounds.