200868-50-4

Upstream product

• 256942-80-0 tert-butyl(cyclohexa-2,5-dien-1-yl)dimethylsilane 
• 90467-12-2 tert-butyldimethylphenylsilane 
• 100-39-0 benzyl bromide 
• 256942-68-4 (1S,2S,3S)-3-[tert-butyl(dimethyl)silyl]cyclohexane-4-ene-1,2-diol 

Downstream Products

• 1026431-53-7 ((1R,2S,3S,4S,6R)-3,4-Bis-benzyloxy-bicyclo[4.1.0]hept-2-yl)-tert-butyl-dimethyl-silane 
• 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 
• 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 
• 200707-95-5 C₂₁H₂₃BrO₂ 
• 200707-77-3 C₂₁H₂₃IO₂ 
• 200707-87-5 (3aS,4S,5S,7R,7aS)-4,5-Bis-benzyloxy-7-bromomethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 200868-54-8 ((3aS,4S,6S,7S,7aS)-6,7-Bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl)-acetaldehyde 
• 200868-52-6 ((1S,4R,5S)-4,5-Bis-benzyloxy-cyclohex-2-enyl)-acetic acid ethyl ester 
• 200707-97-7 ((1R,4R,5S)-4,5-Bis-benzyloxy-cyclohex-2-enylmethyl)-dimethyl-phenyl-silane 
• 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 
• 200707-78-4 Acetic acid (1S,2S,3S,5S,6S)-2-acetoxy-3-acetoxymethyl-5,6-bis-benzyloxy-cyclohexyl 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 
• 200707-84-2 (1S,2S,3R,4S,6R)-3,4-Bis-benzyloxy-6-methyl-cyclohexane-1,2-diol 

Relevant academic research and scientific papers

Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics

Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.

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.