35949-53-2

Upstream product

• 77-95-2 D-(-)-quinic acid 
• 108-94-1 cyclohexanone 
• 933-40-4 cycloxexanone dimethyl ketal 
• 168784-18-7 C₁₃H₂₀O₆ 
• 901129-88-2 methyl 3,5-di-O-(tert-butyldimethylsilyl)-4-O-methanesulfonylquinate 
• 191916-39-9 methyl (-)-quinate 
• 135711-62-5 methyl quinicate 
• 213250-58-9 (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-oxocyclohexanecarboxylic acid methyl ester 

Downstream Products

• 160341-65-1 C₂₀H₂₄O₅ 
• 160341-72-0 C₂₂H₂₇ClO₅ 
• 219547-38-3 (3R,5R)-1-Benzyloxy-3,4,5-trihydroxy-cyclohexanecarboxylic acid amide 
• 219547-37-2 C₂₀H₂₇NO₅ 
• 1899-30-5 trans-3-p-coumaroylquinic acid 
• 25514-46-9 (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid 

Relevant academic research and scientific papers

Construction of the Bicyclic Core Structure of the Enediyne Antibiotic Esperamicin-A1 in Either Enantiomeric Form from (-)-Quinic Acid

Employed as a common chiral starting material, (-)-quinic acid (7) was converted in a concise manner to both enantiomers of the β,γ-unsaturated ketone 12.On the one hand, (+)-12 was obtained by stereospecific borohydride reduction of the conjugated ketone

Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid

(-)-Quinic acid possess eight possible stereoisomers, which occur both naturally and as products of thermal food processing. In this contribution, we have selectively synthesized four isomers, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid, and scyllo-quinic acid, to develop a tandem LC-MS method identifying all stereoisomeric quinic acids. Four derivatives have been unambiguously characterized by single-crystal X-ray crystallography. The missing diastereomers of quinic acid were obtained by nonselective isomerization of (-)-quinic acid using acetic acid/concentrated H2SO4 allowing chromatographic separation and assignment of all diastereomers of quinic acid. We report for the first time that a full set of stereoisomers are reliably distinguishable on the basis of their tandem mass spectrometric fragment spectra as well as their elution order. A rationale for characteristic fragmentation mechanisms is proposed. In this study, we also observed that muco-quinic acid, scyllo-quinic acid, and epi-quinic acid are present in hydrolyzed Guatemalan roasted coffee sample as possible products of roasting.

Novel compound, its synthetic method and therapeutic use (by machine translation)

Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.

Stereoselective synthesis of the halaven C14-C26 fragment from D-quinic acid: Crystallization-induced diastereoselective transformation of an α-methyl nitrile

Crystallization-induced diastereoselective transformation (CIDT) of an α-methyl nitrile completes an entirely non-chromatographic synthesis of the halichondrin B C14-C26 stereochemical array. The requisite α-methyl nitrile substrate is derived from D-quinic acid through a series of substrate-controlled stereoselective reactions via a number of crystalline intermediates that benefit from a rigid polycyclic template. Therefore, all four stereogenic centers in the Halaven C14-C26 fragment were derived from the single chiral source D-quinic acid.

Parallel synthesis and biological evolution of quinic acid derivatives as immuno-suppressing agents against T-cell receptors

A simple protocol for the synthesis of quinic acid derivatives was established and their biological evolution against T-cells is studied. Results showed that one of the derivatives, Cyn-1324, has low toxicity on T-cells and a high effect on reducing Signal 2 of T-cell immune responses. In vitro binding measurements of atomic force spectroscopy further indicated that the blocking effect of Cyn-1324 between CD28 and CD80 was about 31 ± 4%. In vivo animal tests also confirmed that Cyn-1324 can reduce the allergic responses from ovalbumin-induced mice with little toxicity. Based on these observations, Cyn-1324 can be a mild immuno-suppressive candidate for future drug development.

Synthesis and HIV-1 inhibitory activities of dicaffeoyl and digalloyl esters of quinic acid derivatives

Twenty analogues of the anti-HIV-1 integrase (IN) inhibitors dicaffeoylquinic acids (DCQAs) were prepared. Their IC50 values for 3'-end processing and strand transfer against recombinant HIV-1IN were determined in vitro, and their cell toxiciti

The synthesis of 2-oxyalkyl-cyclohex-2-enones, related to the bioactive natural products COTC and antheminone A, which possess anti-tumour properties

The syntheses of five novel 2-oxyalkyl-cyclohex-2-enones, structurally related to the natural products COTC and antheminone A, are described. The target structures were selected in order to probe the influence of several key structural parameters on in vi

CAFFEOYL QUINIC ACID DERIVATIVES CONTAINING NITROGEN, AND PREPARATION METHOD, PHARMACEUTICALLY COMPOSITION AND USAGE THEREOF

The present invention provides caffeoylquinic acid derivatives and a method of preparing for the same, and also provides pharmaceutical compositions containing caffeoylquinic acid derivatives, and uses of caffeoylquinic acid derivatives in preparation of

(-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties

Syntheses of three novel analogues of the Streptomyces metabolite COTC are described, using the versatile chiral pool starting material, (-)-quinic acid. The results of bioassays of the target compounds against two lung cancer cell lines, A549 and H460, a

INTERMEDIATES FOR THE PREPARATION OF HALICHONDRIN B

The present invention provides macrocyclic compounds, synthesis of the same and intermediates thereto. Such compounds, and compositions thereof, are useful for treating or preventing proliferative disorders Formula (F-4).