200707-77-3

Upstream product

• 200868-50-4 (1S,2S,3S)-1,2-dibenzyloxy-3-tert-butyldimethylsilylcyclohex-4-ene 
• 1026431-53-7 ((1R,2S,3S,4S,6R)-3,4-Bis-benzyloxy-bicyclo[4.1.0]hept-2-yl)-tert-butyl-dimethyl-silane 

Downstream Products

• 94943-07-4 (1S,2S,3S,4S,5S)-5-(acetoxymethyl)cyclohexane-1,2,3,4-tetrayl tetraacetate 
• 200728-85-4 (1S,2S,3S,4S,5R)-5-Methyl-cyclohexane-1,2,3,4-tetraol 
• 200707-78-4 Acetic acid (1S,2S,3S,5S,6S)-2-acetoxy-3-acetoxymethyl-5,6-bis-benzyloxy-cyclohexyl ester 
• 200707-84-2 (1S,2S,3R,4S,6R)-3,4-Bis-benzyloxy-6-methyl-cyclohexane-1,2-diol 
• 200707-97-7 ((1R,4R,5S)-4,5-Bis-benzyloxy-cyclohex-2-enylmethyl)-dimethyl-phenyl-silane 

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.

Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes

A synthesis of pseudo-sugars using the desymmetrization of a dienylsilane, followed by a stereocontrolled introduction of the hydroxymethyl group at C5, is described. The CH2OH group at C5 was elaborated using either a regioselective cyclopropane-ring opening or a [2,3]-Wittig rearrangement.