215370-49-3

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 215370-46-0 (1S,3R,4R)-1-methoxycarbonyl-cyclohexane-1,3,4-triol 
• 215370-45-9 Benzoic acid (1S,4R,5R)-1-hydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester 
• 105539-78-4 (1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate 

Downstream Products

• 1053729-00-2 Toluene-4-sulfonic acid (1S,2S,3S,4R)-1,2-dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexylmethyl ester 
• 215370-55-1 (1R,2S,3S,4R)-1,2-Dihydroxy-3-methoxy-4-triethylsilanyloxy-cyclohexanecarboxylic acid methyl ester 
• 215370-54-0 (3S,4R)-3-Methoxy-4-triethylsilanyloxy-cyclohex-1-enecarboxylic acid methyl ester 
• 215370-52-8 (3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohex-1-enecarboxylic acid methyl ester 
• 215370-56-2 (1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol 
• 215370-53-9 (3S,4R)-4-hydroxy-1-methoxycarbonyl-3-methyloxy-cyclohex-1-ene 
• 215370-51-7 (3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective formal synthesis of (-)-ovalicin using quinic acid as a chiral template

The key intermediate 18 for the synthesis of (-)-ovalicin was synthesized using (-)-quinic acid as the chiral source, through a series of stereocontrolled and efficient chemical reactions, thus establishing a new, formal synthesis of the natural target. The featuring spirocyclic epoxide function has been installed by internal Williamson ether synthesis using the functionalities originally present at C-1 of (-)-quinic acid after the appropriate adjustments required to introduce the necessary functionality at C-2.