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Upstream product

• 98933-74-5 tributyl-(3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexapyranosyl)stannane 
• 441044-62-8 methyl 6-S-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 252851-40-4 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-mercapto-α-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.

Reversal of anomeric selectivity with O-glycosyl trichloroacetimidates as glycosyl donors and thiols as acceptors under acid/base catalysis

Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O-glucopyranosyl or O-galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α-thioglycosides. However, the same reaction