183134-52-3

Upstream product

• 67-56-1 methanol 
• 665-27-0 1,5-quinide 
• 850353-75-2 methyl (1R,3R,4S)-3,4-O-cyclohexylidene-1,3,4-trihydroxycyclohexanecarboxylate 
• 183134-51-2 (2R,3aR,5S,7aS)-5-Benzyloxycarbonyloxy-2-phenyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 94903-42-1 (1R,2R,4R,6R,8S)-8-Hydroxy-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undecan-9-one 
• 77-95-2 D-(-)-quinic acid 
• 130021-73-7 methyl 3,4-O-cyclohexylidenequinate 
• 850353-73-0 methyl (1R,3R,4S,5R)-3,4-O-cyclohexylidene-5-(1H-imidazole-1-carbonothioyloxy)-1,3,4-trihydroxycyclohexanecarboxylate 
• 850353-98-9 (1R,3R,4S)-3,4-O-isopropylidene-1-hydroxymethyl-1-hydroxycyclohexan-3,4-diol 
• 183134-50-1 (2R,3aR,5R,7R,7aS)-5-Benzyloxycarbonyloxy-7-hydroxy-2-phenyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 183134-49-8 Carbonic acid benzyl ester (1R,2R,4R,6R,8S)-9-oxo-4-phenyl-3,5,10-trioxa-tricyclo[6.2.1.0^2,6]undec-8-yl ester 

Downstream Products

• 183134-53-4 (1R,4S)-1,4-Dihydroxy-3-oxo-cyclohexanecarboxylic acid 
• 183254-44-6 (S)-4-Hydroxy-3-oxo-cyclohex-1-enecarboxylic acid 

Relevant academic research and scientific papers

Deoxygenative Divergent Synthesis: En Route to Quinic Acid Chirons

The installation of vicinal mesylate and silyl ether groups in a quinic acid derivative generates a system prone for stereoselective borane-catalyzed hydrosilylation through a siloxonium intermediate. The diversification of the reaction conditions allowed the construction of different defunctionalized fragments foreseen as useful synthetic fragments. The selectivity of the hydrosilylation was rationalized on the basis of deuteration experiments and computational studies.

Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H 1]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2- 2H1]-homocitrate lactones - An assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V protein

Trimethyl (3R)-homocitrate 17, trimethyl (2S,3R)-[2-2H 1]-homocitrate 17a and (2R,3R)-[2-2H1]- homocitrate 17b, as well as dimethyl (3R)-homocitrate lactone 18, (2S,3R)-[2-2H1]-homocitric lactone 18a and (2R,3R)-[2-2H1]-homocitric lactone 18b have been synthesised. d-Quinic acid 12 was used as the source of the (3R)-centre in the unlabelled target compounds 17 and 18. (-)-Shikimic acid 19 and the (-)-[2- 2H]-shikimic acid derivative 32 respectively were used in the synthesis of the labelled compounds. In the latter syntheses, Sharpless directed epoxidation of the olefin in the 5-deoxy ester diols 23 and 35 ensured a reaction from the same face as the allylic and homoallylic alcohols, and the reduction of the protected epoxides 25 and 37 ensured that the label was introduced in a stereoselective manner. The 1H NMR spectra of the labelled products present an assay for the stereochemistry of the biological reactions catalysed by homocitrate synthase and by the protein from the nifV gene. The Royal Society of Chemistry 2006.

Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H 1]-homocitrates and the corresponding dimethyl ester lactones-towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein

Trimethyl (2S,3R)- and (2R,3R)-[2-2H1]-homocitrates, 10b and 10c respectively, and dimethyl (2S,3R)- and (2R,3R)-[2- 2H1]-homocitric lactones, 11b and 11c respectively, have been synthesised from shikimic acid a

Comparison of the substrate specificity of type I and type II dehydroquinases with 5-deoxy- and 4,5-dideoxy-dehydroquinic acid

Syntheses of 5-deoxydehydroquinic acid and 4,5-dideoxydehydroquinic acid from quinic acid are described. These substrate analogues were tested against the mechanistically-distinct type I and type II dehydroquinases. The C-4 hydroxy group of the substrate is shown to be important for imine formation on the type I enzyme but appears not to contribute significantly to specificity on the type II dehydroquinase.