1256137-67-3

Upstream product

• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1256137-62-8 methyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside 
• 1256137-72-0 C₂₂H₃₃BrO₇Si 

Downstream Products

• 1256138-02-9 C₂₂H₃₂O₇Si 

Relevant academic research and scientific papers

Carbene-mediated functionalization of the anomeric C-H bond of carbohydrates: Scope and limitations

Herein we investigate the scope and limitations of a new synthetic approach towards α- and β-ketopyranosides relying on the functionalization of the anomeric C-H bond of carbohydrates by insertion of a metal carbene. A key bromoacetate grafted at the 2-position is the cornerstone of a stereoselective glycosylation/diazotransfer/quaternarization sequence that makes possible the construction of a quaternary center with complete control of the stereochemistry. This sequence shows a good tolerance toward protecting groups commonly used in carbohydrate chemistry and gives rise to quaternary disaccharides with good efficiency. In the case of a disaccharide with a more restricted conformation, this functionalization process can be hampered by the steric demand next to the targeted anomeric position. In addition, the formation of transient orthoesters during the glycosylation step may also reduce the overall efficiency of the synthetic sequence. Copyright

Rh(II) carbene-mediated synthesis of methyl α- And β-ketopyranosides: Preparation of carbene precursors, quaternarization of the anomeric position, and ring opening of γ-lactones

Methyl α- and β-ketopyranosides were efficiently prepared by carbene-mediated quaternarization of the anomeric position of corresponding aldopyranosides. Preparation of carbene precursors proved to be tedious and required a two-step procedure involving fi

Rh(II) carbene-promoted activation of the anomeric C-H bond of carbohydrates: A stereospecific entry toward α- And β-ketopyranosides

In this communication we report a new strategy toward ketopyranosides based on a carbene-mediated activation of the anomeric C-H bond of carbohydrates. By forming a new carbon-carbon bond after a glycosylation step, this approach enables the preparation o