188981-72-8

Upstream product

• 51-79-6 urethane 
• 179749-34-9 Cyclohexa-2,5-dienyl-dimethyl-silanol 
• 17510-52-0 sodium chloro(ethoxycarbonyl)chloroamide 

Downstream Products

• 188981-81-9 ((1R,2S)-2-Hydroxy-cyclohexyl)-carbamic acid ethyl ester 
• 188981-78-4 (3aR,4R,5aS,8aS,8bR)-4-Iodo-7,7-dimethyl-2-oxo-3-(toluene-4-sulfonyl)-octahydro-benzo[1,2-d;3,4-d']bisoxazole-8-carboxylic acid ethyl ester 
• 256942-75-3 (1S,2S,3S)-2-N-ethoxycarbonylcyclohex-4-ene-1,3-diol 

Relevant academic research and scientific papers

Asymmetric amino-hydroxylation of dienylsilanes. An efficient route to amino-cyclitols

Sharpless asymmetric amino-hydroxylation of a silyl-2,5-cyclohexadiene occurs with complete regio- and diastereocontrol. An enantioselectivity of up to 68% e.e. was also observed. An application of the methodology to the synthesis of relevant examples of amino-cyclitols is described.

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.