200868-52-6

Upstream product

• 200868-50-4 (1S,2S,3S)-1,2-dibenzyloxy-3-tert-butyldimethylsilylcyclohex-4-ene 
• 200868-51-5 (1S,2S,3S,4S,6S,7S)-3,4-Bis-benzyloxy-2-(tert-butyl-dimethyl-silanyl)-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester 

Downstream Products

• 200868-54-8 ((3aS,4S,6S,7S,7aS)-6,7-Bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl)-acetaldehyde 
• 200868-53-7 ((3aS,4S,6S,7S,7aS)-6,7-Bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl)-acetic acid ethyl ester 
• 200868-60-6 1-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-2-((3aS,4R,6S,7S,7aS)-6,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl)-ethanol 

Relevant academic research and scientific papers

Desymmetrisation of dienylsilanes. Stereoselective access to cyclitols and carba-sugars

The diastereo- and enantioselective functionalisation of 1,4-cyclohexadienylsilanes using Sharpless asymmetric dihydroxylation and aminohydroxylation offers a straightforward access to various classes of potent inhibitors of glycosidases. The scope and limitation of this desymmetrisation method is illustrated here with the synthesis of various conduritols, carba-sugars and carba-C-disaccharides.

Stereocontrolled access to carba-C-disaccharides via functionalized dienylsilanes

We report here the total synthesis of a class of C1 → C6 Carba-C-disaccharide, formed by the association between a 2-deoxyglucose as the sugar unit and a pseudo-pyranose or a pseudo-furanose as the carba-sugar moiety. The carba-sugar fragments were assembled from the corresponding dienylsilanes through a dihydroxylation-cyclopropanation sequence.