623157-48-2

Upstream product

• 691371-32-1 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-furanyl)ethanone 
• 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 
• 100-51-6 benzyl alcohol 
• 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 

Downstream Products

• 679411-88-2 (1S,5S)-1-benzyloxy-5-hydroxymethyl-1H-pyran-4-one 
• 1385024-28-1 (2S,3R,6R)-6-(benzyloxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol 
• 1385024-29-2 (2S,6R)-6-(((2S,3R,6R)-6-(benzyloxy)-2-((((2R,6S)-6-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-2H-pyran-3(6H)-one 
• 1385024-30-5 (2S,3R,6R)-6-(((2S,3R,6R)-6-(Benzyloxy)-2-((((2R,5R,6S)-6-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-ol 
• 1385024-31-6 (2S,3R,6R)-6-(((2S,3R,6R)-6-(benzyloxy)-2-((((2R,5R,6S)-5-hydroxy-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-yl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl)oxy)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol 
• 1442690-49-4 C₁₃H₁₇N₃O₅ 
• 1442690-52-9 C₁₃H₁₇N₃O₅ 
• 1442690-42-7 C₁₃H₁₈O₆ 
• 1442690-39-2 (1R,2S,4R,5R,6S)-4-(benzyloxy)-2-(hydroxymethyl)-3,7-dioxabicyclo[4.1.0]heptan-5-ol 
• 1442690-38-1 (1R,2S,4R,5R,6S)-4-(benzyloxy)-2-(tert-butyldimethylsilyloxymethyl)-3,7-dioxabicyclo[4.1.0]heptan-5-ol 
• 1442690-34-7 (2R,3R,6R)-2-(benzyloxy)-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-ol 
• 1442690-33-6 (1R,2R,4S,6S)-2-(benzyloxy)-4-(tert-butyldimethylsilyloxymethyl)-3,7-dioxabicyclo[4.1.0]heptan-5-one 
• 679412-00-1 6-[6-[6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-ol 
• 679411-98-4 6-[6-[6-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yloxy]-2-(tert-butyl-dimethyl-silanyloxymethyl)-6H-pyran-3-one 

Relevant academic research and scientific papers

Application of the Wharton rearrangement for the de novo synthesis of pyranosides with ido, manno, and colito stereochemistry

A de novo asymmetric synthesis of α-ido-pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)-catalyzed glycosylation in combination with a Wharton rearrangement/epoxide-opening reaction sequence to access sugars with ido, manno, and colito stereochemistry as well as several azido analogues. A de novo asymmetric synthesis of α-ido-pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)- catalyzed glycosylation in combination with a Wharton rearrangement/epoxide- opening reaction sequence to access sugars with ido, manno, and colito stereochemistry as well as several azido analogues. Copyright

De novo asymmetric synthesis of All-d-, All-l-, and d-/l-oligosaccharides using atom-less protecting groups

Oligosaccharide synthesis is hindered by the need for multiple steps as well as numerous selective protections and deprotections. Herein we report a highly efficient de novo route to various oligosaccharide motifs, of use for biological and medicinal structure activity studies. The key to the overall efficiency is the judicious use of asymmetric catalysis and synthetic design. These green principles include the bidirectional use of highly stereoselective catalysis (Pd(0)-catalyzed glycosylation/post-glycosylation). In addition, the chemoselective use of C-C and C-O π-bond functionality, as atom-less protecting groups as well as an anomeric directing group (via a Pd-π-allyl), highlights the atom-economical aspects of the route to a divergent set of natural and unnatural oligosaccharides (i.e., various d-/l-diastereomers of oligosaccharides as well as deoxysugars which lack C-2 anomeric directing groups). For example, in only 12 steps, the construction of a highly branched heptasaccharide with 35 stereocenters was accomplished from an achiral acylfuran.

De Novo Synthesis of Oligosaccharades Using a Palladium-Catalyzed Glycosylation Reaction

The natural all d- and/or unnatural all l-1,4- and 1,6-oligosaccharides were synthesized from furan alcohols using a palladium-catalyzed glycosylation reaction. The 1,4- and 1,6-α-manno-disaccharides were achieved in seven total steps starting from chiral furan alcohols. Similarly, 1,4- and 1,6-α-manno-trisaccharides were also synthesized in nine total steps. Key to the overall efficiency of this process was the use of highly diastereoselective palladium-catalyzed glycosylations, reductions, and dihydroxylations. Copyright

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