623157-52-8

Upstream product

• 623157-43-7 (2S,6S)-carbonic acid tert-butyl ester 6-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-2,3-dihydro-6H-pyran-2-yl ester 
• 302348-82-9 (2S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2H-pyran-3(6H)-one 
• 222986-37-0 (S)-2-((tert-butyldimethylsilyl)oxy)-1-(furan-2-yl)ethan-1-ol 
• 623157-51-7 (2'S,2S,6R)-6-[2'-benzyloxycarbonylamino propionoic acid methyl ester-1'-yloxy]-2-tert-butyldimethylsilanyloxy-6H-pyran-3-one 

Relevant academic research and scientific papers

A palladium-catalyzed glycosylation reaction: The de novo synthesis of natural and unnatural glycosides

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