32384-44-4

Upstream product

• 100-52-7 benzaldehyde 
• 77-95-2 (1R,3R,4S)-1,3,4,5-Tetrahydroxy-cyclohexanecarboxylic acid 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 105539-78-4 (1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate 
• 124561-23-5 (3R,4S,5R)-3,4-O,O'-benzylidene-1-(hydroxymethyl)cyclohexane-1,3,4,5-tetrol 
• 94903-41-0 (-)-methyl 4,5-O-benzylidene-4-epi-shikimate 
• 94903-43-2 (1S,2S,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-en-2-ol 
• 94843-97-7 (1R,2R,6R,8S)-2-(benzoyloxy)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene 
• 94843-96-6 (1S,4S,6R,8S)-4-(methoxycarbonyl)-2-oxo-8-phenyl-7,9-dioxabicyclo<4.3.0>nonan-4-ol 
• 21967-35-1 (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 
• 94843-95-5 (1S,2R,4R,6R,8S)-4-(methoxycarbonyl)-8-phenyl-7,9-dioxabicyclo<4.3.0>nonane-2,4-diol 

Relevant academic research and scientific papers

Application of stereocontrolled aldol coupling to synthesis of segments of immunosuppressants FK-506 and rapamycin

The sector comprising C24-C34 of FK-506 containing five of the stereogenic centers in this macrolide was synthesized from (-)-quinic acid. Aldol coupling of the C24-C34 unit with a methyl ketone representing C20-C23 of FK-506 proceeded with complete Felkin stereoselectivity to afford the C20-C34 portion of the immunosuppressant. A chelate transition state invoking coordination of a lithium enolate with a trityl ether is proposed to explain this stereoselectivity. The strategy adopted for construction of the C26-C34 moiety of FK-506 was extended to the C34-C42 subunit of rapamycin. A Mukaiyama asymmetric anti-aldol coupling was used to set in place the vicinal diol functionality at C27,28 in the C26-C33 segment of this macrolide.

Synthesis of (2R)-2-bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid

(2R)-2-Bromodehydroquinic acid and (2R)-2-fluorodehydroquinic acid ? have each been synthesised in six steps from quinic acid via the common intermediate 6. The syntheses exploit the selective protection of the 4-hydroxy group of the quinic acid lactone 3 with tert-butyldimethylsilyl chloride. ? IUPAC names: (1S,2R,4S,5R)-2-bromo-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid and (1S,2R,4S,5R)-2-fluoro-1,4,5-trihydroxy-3-oxocyclohexanecarboxylic acid, respectively.

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.

13C and 1H NMR Investigations of Quinic Acid Derivatives: Complete Spectral Assignment and Elucidation of Preferred Conformations

The 1H and 13C NMR spectra of 23 quinic acid derivatives are reported.The complete assignment of the 1H NMR spectra using selective proton decoupling experiments allowed the conformation of the six membered ring to be established from vicinal coupling con