172847-95-9

Upstream product

• 100-39-0 benzyl bromide 
• 696-63-9 4-Methoxybenzenethiol 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 

Downstream Products

• 172880-26-1 p-Methoxyphenylmethyl 2-acetamido-6-O-benzyl-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 172880-25-0 p-Methoxyphenylmethyl 2-acetamido-4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

Stereoretentive C(sp3)-S Cross-Coupling

We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functionalities under standardized conditions. Competition experiments in combination with computational DFT studies established that the putative anomeric intermediate is an organocopper species that is configurationally stable and resistant to epimerization due to its short lifetime. The subsequent reductive elimination from the Cu(III) intermediate is rapid and stereoretentive. Taken together, the glycosyl cross-coupling is ideally suited for late stage glycodiversification and bioconjugation under highly controlled installation of the aliphatic carbon-sulfur bonds.

THIOGLYCOSIDES AS POTENTIAL GLYCOSYL DONORS IN ELECTROCHEMICAL GLYCOSYLATION REACTIONS. PART 1: THEIR PREPARATION AND REACTIVITY TOWARD SIMPLE ALCOHOLS

Costant potential electrolysis of several glycosyl donors such as substituted phenyl 2,3,4,6-tetra-O-acetyl, benzoyl or benzyl-1-thio-β-D-gluco or galactopyranosides in dry acetonitrile in the presence of various primary, secondary or tertiary alcohols performed in an undivided cell, gave preferentially β-linked saccharides in moderate to good yields according to the nature of the protective groups on the sugar moiety. 2-Deoxy-2-phthalimido-1-thio-β-D-gluco derivatives gave the β-glucosides selectively in excellent yields.It was found, as expected, that substitution of the phenyl group with methoxy or methyl radicals facilitates the electrochemical glycosylation reaction by lowering the oxidation potentials of the corresponding thioglycosides.