92051-20-2

Upstream product

• 19879-84-6 tetraacetyl thioglucose 
• 79580-70-4 Methyl 2,3,6-tri-O-benzoyl-4-O-trifluoromethanesulfonyl-α-D-galactopyranoside 
• 108-24-7 acetic anhydride 

Downstream Products

• 92051-21-3 1-O-acetyl-2,3,6-tri-O-benzoyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-α,β-D-glucopyranose 

Relevant academic research and scientific papers

From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides

The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.

4-Thiocellooligosaccharides. Their synthesis and use as ligands for the separation of cellobiohydrolases of Trichoderma reesei by affinity chromatography

4-Aminophenyl 1,4-dithio-β-cellobioside (6) was obtained by treatment of methyl 2,3,6-tri-O-benzoyl-4-O-triflyl-α-D-galactopyranoside with sodium salt of 1-thio-β-D-glucopyranose, followed by acetolysis and glycosylation of the corresponding bromide with

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)

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.