57764-14-4

Upstream product

• 67-56-1 methanol 
• 10534-44-8 3-dehydroquinic acid 
• 176798-26-8 (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 77-95-2 D-(-)-quinic acid 
• 183474-88-6 methyl (1S,4S,5R)-1-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-3-oxo-cyclohexan-1-carboxylate 

Downstream Products

• 134252-19-0 4,5-bis-O-trimethylsilyl-3-deshydroshikimate de methyle 
• 134252-20-3 1,4,5-tris-O-trimethylsilyl-3-deshydroquinate de methyle 
• 2150-43-8 3,4-dihydroxybenzoic acid methyl ester 
• 84806-48-4 methyl (4S,5R)-4,5-dihydroxy-3-oxo-1-cyclohexene-1-carboxylate 
• 494211-77-7 methyl (1R,4S,5R)-4,5-bis(benzoyloxy)-1-hydroxy-3-oxocyclohexane-1-carboxylate 
• 494211-81-3 methyl (1S,3E,4R,5R)-3-(hydroxyimino)-1,4,5-trihydroxycyclohexane-1-carboxylate 
• 10534-44-8 3-dehydroquinic acid 
• 494211-78-8 C₂₂H₂₁NO₈ 
• 203920-81-4 (1R,3S,4S,5R)-3-Hydroxy-3-prop-2-ynyl-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester 
• 203920-77-8 (1R,3R,4S,5R)-3-Ethoxycarbonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester 
• 203920-79-0 (1R,3S,4S,5R)-3-Benzenesulfonylmethyl-3-hydroxy-1,4,5-tris-trimethylsilanyloxy-cyclohexanecarboxylic acid methyl ester 

Relevant academic research and scientific papers

A convenient method for the synthesis of dehydroquinic acid

A convenient synthesis of dehydroquinic acid and its corresponding methyl ester are described. Protection of the trans diol of quinic acid, followed by PCC oxidation, gave fully protected dehydroquinic acid. This gave methyl dehydroquinate on mild acid ca

Stereoselectivity in Nucleophilic Additions to the Carbonyl Group of Methyl 1,4,5-tris(trimethylsilyl)-3-dehydroquinate

Methyl 1,4,5-tris(trimethylsilyl)-3-dehydroquinate was synthesized in a three-step procedure and condensed with various nucleophiles (-CH2COOEt, -CH2SO2Ph, -CH2-CCH, H-).The diastereoselectivity of the reaction, leading to the creation of a new quaternary (or tetiary) asymmetric carbon atom was examined.The preferential axial attack on the C=O group of the cyclohexanone system is discussed.The deprotected products were evaluated as DHQase inhibitors. - Keywords: methyl 3-dehydroquinate; nucleophilic addition; diastereoselectivity.