1026431-53-7

Upstream product

• 75-11-6 diiodomethane 
• 200868-50-4 (1S,2S,3S)-1,2-dibenzyloxy-3-tert-butyldimethylsilylcyclohex-4-ene 
• 256942-68-4 (1S,2S,3S)-3-[tert-butyl(dimethyl)silyl]cyclohexane-4-ene-1,2-diol 
• 256942-80-0 tert-butyl(cyclohexa-2,5-dien-1-yl)dimethylsilane 
• 90467-12-2 tert-butyldimethylphenylsilane 

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 
• 200707-87-5 (3aS,4S,5S,7R,7aS)-4,5-Bis-benzyloxy-7-bromomethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 200707-97-7 ((1R,4R,5S)-4,5-Bis-benzyloxy-cyclohex-2-enylmethyl)-dimethyl-phenyl-silane 
• 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 
• 200707-77-3 C₂₁H₂₃IO₂ 
• 200707-95-5 C₂₁H₂₃BrO₂ 

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.