PHASE-TRANSFER CATALYSED SYNTHESIS OF 4-S-β-D-GLUCOPYRANOSYL-4-THIO-D-GLUCOPYRANOSE (THIOCELLOBIOSE) AND 2-S-β-D-GLUCOPYRANOSYL-2-THIO-D-GLUCOPYRANOSE (THIOSOPHOROSE)

Article abstract of DOI:10.1016/0008-6215(84)85336-7

Syntheses of the potential enzyme-inducers thiocellobiose (7) and thiosophorose (11) ara described.The intermediates methyl 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-α-D-galactopyranoside and 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethylsulfonyl-β-D-mannopyranose were obtained in good yield from methyl α-D-galactopyranoside or 1,3,4,6-tetra-O-acetyl-β-D-mannopyranose.The stereoselective reaction of triflates with the sodium salt of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose was performed under phase-transfer conditions.Transesterification of methyl 2,3,6-tri-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-β-D-glucopyranoside (after selective acetolysis) and 1,3,4,6-tetra-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thio-β-D-glucopyranose afforded 7 and 11.