887326-75-2Relevant academic research and scientific papers
A palladium-catalyzed glycosylation reaction: The de novo synthesis of natural and unnatural glycosides
Babu, Ravula Satheesh,O'Doherty, George A.
, p. 12406 - 12407 (2003)
A highly stereoselective and sterospecific palladium-catalyzed glycosylation reaction of a variety of alcohols is reported. The reaction selectively converts α-2-substituted 6-carboxy-2H-pyran-3(6H)-ones into α-2-substituted 6-alkoxy-2H-pyran-3(6H)-ones with complete retention of configuration and similarly converts the pyranones with β-carboxy groups into pyranones with β-alkoxy groups. The reaction works equally well with both amino acid- and carbohydrate-based alcohols. To demonstrate the utility of this process for carbohydrate chemistry several of the products were selectively converted into α-manno-pyranosides in two additional steps. Because the 2-substituted 6-carboxy-2H-pyran-3(6H)-ones are prepared by asymmetric synthesis, this reaction can be used for the preparation of either d- or l-pyranones. Copyright
Synthetic studies toward mannopeptimycin-E: Synthesis of the O-linked tyrosine 1,4-α,α-manno,manno-pyranosyl pyranoside
Babu, Ravula Satheesh,Guppi, Sanjeeva R.,O'Doherty, George A.
, p. 1605 - 1608 (2007/10/03)
The enantioselective synthesis of the C-4′ acylated 1,4-α,α-manno,manno-disaccharide fragment of mannopeptimycin-E has been achieved in seven steps from D-tyrosine. The route relies upon diastereoselective palladium-catalyzed glycosylation, diastereoselec
