68703-54-8

Upstream product

• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 76-83-5 trityl chloride 
• 19879-84-6 tetraacetyl thioglucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 68703-52-6 S-trityl-1-thio-β-D-glucopyranose 
• 72174-24-4 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-thiol 
• 247257-17-6 (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 857657-51-3 triphenylmethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 857657-62-6 2-bromo-2-methylpropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 857657-59-1 2-hydroxy-2-methylpropyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 857657-42-2 triphenylmethyl 2,3,4,6-tetra-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 857657-43-3 triphenylmethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 857892-35-4 triphenylmethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Modified one-pot protocol for the preparation of thioglycosides from unprotected aldoses via S-glycosyl isothiouronium salts

An efficient one-pot protocol for the direct preparation of thioglycosides starting from unprotected reducing sugars via S-glycosyl isothiouronium salts is reported. In this one-pot methodology, BF3·OEt2 has been used as a general catalyst for both per-O-acetylation of sugars and conversion of sugar per-O-acetates into S-glycosyl isothiouronium salts, which was allowed to react with alkylating agents in the presence of a base to furnish thioglycosides in excellent yield. Copyright Taylor & Francis, Inc.

2-Haloethyl 1-thioglycosides as new tools in glycoside syntheses. Part 1: Preparation, characteristics, general reactions

2-Haloethyl 1-thioglycosides are excellent leaving groups when the 2-haloethyl function is activated with silver salts or Lewis acids. These thioglycosides can be synthesized on the original Cerny route or for better compatibility with the needs of a more complex glycoside synthesis, in stepwise procedures via 2-(2-tetrahydropyran-2-yloxy)ethyl glycosides or trityl 1-thioglycosides. The initial step in glycosidation reaction presumably proceeds via a thiiranium ion, which is responsible for their increased reactivity compared with normal thioethers as leaving groups in glycoside syntheses. Basic features of this new system with respect to reactivity and selectivity in disaccharide syntheses are described.

A general procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides, thiooligosaccharides and glycosyl thioesters

A simple procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides by promotion with triethylamine is described. The reaction conditions allow the synthesis of glycosyl thioesters and some thioglycosides, which cannot be prepared using the traditional approach. The procedure has been successfully applied for preparation of thiooligosaccharides, shown by syntheses of methyl 4-thio-α-cellobioside and methyl 4-thio-α-lactoside derivatives.

Tri-substituted phosphinegold(I) 1-thio-β-D-glucopyranosides

The compounds are tri-substituted phosphinegold(I) 1-thio-β-D-glucopyranosides which have antiarthritic activity and, in particular, are of use in the treatment of rheumatoid arthritis. Of the three substituents on the phosphine one is optionally substituted phenyl and the others are lower alkyl or lower alkoxy.

Process for preparing auranofin

Auranofin and its congeners are prepared by the reaction of a S-substituted 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose with a tertiary phosphine gold ester or sulfide.

Method for preparing auranofin

Bis(triethylphosphine)gold salts are advantageous agents for preparing auranofin.