1174754-24-5

Upstream product

• 100-51-6 benzyl alcohol 
• 41728-14-7 6-hydroxy-2-methyl-2H-pyran-3(6H)-one 
• 1192-62-7 1-(2-furyl)-1-ethanone 
• 4208-64-4 1-(2-furyl)ethanol 
• 865484-73-7 tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate 
• 512809-21-1 benzyl 2,3,6-trideoxy-α-L-hex-2-enopyranosid-4-ulose 

Downstream Products

• 1174754-22-3 (1R,2R,4S,5S,6R)-2-(benzyloxy)-4-methyl-3,7-dioxabicyclo-[4.1.0]heptan-5-ol 
• 1174754-25-6 (2R,3R,4S,5R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1174754-26-7 (2R,3R,5R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,5-diol 
• 71731-74-3 (2R,3S,4R,5S,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1335126-18-5 (2R,3S,4S,5R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1334606-85-7 (2R,3R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-ol 
• 1334606-94-8 (2R,3R,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol 
• 727414-86-0 (2R,6S)-2-(benzyloxy)-6-methyl-2H-pyran-3(6H)-one 
• 1334607-00-9 (2R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-ol 
• 1334607-07-6 (2R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl pivalate 
• 1334607-11-2 (((2R,6S)-2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran-3-yl)oxy)(tert-butyl)dimethylsilane 
• 1334607-15-6 (2R,3S,6S)-2-(benzyloxy)-6-methyltetrahydro-2H-pyran-3-ol 
• 1334607-28-1 (2R,3S,4R,5S,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate 
• 1334607-25-8 (2R,3S,4S,5R,6S)-2-(benzyloxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl pivalate 

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 synthesis of deoxy sugar via a Wharton rearrangement

A highly divergent synthesis of α-fuco-, α-6-deoxy-allo-, α-6-deoxy-altro-pyranosides has been achieved. This route utilizes a Wharton rearrangement as part of a new post-glycosylation transformation strategy.

De novo asymmetric synthesis of an α-6-deoxyaltropyranoside as well as its 2-/3-deoxy and 2,3-dideoxy congeners

(Chemical Equation Presented) A highly divergent de novo asymmetric synthesis of benzyl α-6-deoxyaltropyranoside, benzyl Rascarylopyranoside, benzyl α-amicetopyranoside, and benzyl α-digitoxopyranoside has been achieved via a common pyranone intermediate. The routes rely upon a palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations. The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers.