Synthesis of methyl 4-thio-β-cellobioside. A reinvestigation

Article abstract of DOI:10.1016/S0008-6215(97)00046-3

The best yield for the synthesis of the title compound was obtained by nucleophilic displacement of the di-O-triflyl group in methyl tri-O-benzyl-4-O-triflyl-β-D-galactopyranoside by 2,3,4,6-tetra-O-acetyl-1-S-acetyl-1-thio-β-D-glucopyranose in HMPA in the presence of diethylamine. Under these conditions, the formation of unsaturated side products was decreased.