2009
DOI: 10.1016/j.tetlet.2008.11.052
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Synthesis and comparative spectroscopic analysis of two chenodeoxycholic acid (CDCA) derivatives with closely related 7α-ester moieties

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Cited by 5 publications
(6 citation statements)
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“…For example, chenodeoxycholic methyl ester was prepared using methanol and p-toluensulfonic acid 27 or methanesulfonic acid 28 and also applying these conditions under microwave irradiation. 29 CDCA ethyl ester was described as an intermediate in the synthesis of chenodiol by reduction of (5β,7α)-7-hydroxy-3-oxocholan-24-oic acid ethyl ester.…”
Section: Enzymatic Esterificationmentioning
confidence: 99%
“…For example, chenodeoxycholic methyl ester was prepared using methanol and p-toluensulfonic acid 27 or methanesulfonic acid 28 and also applying these conditions under microwave irradiation. 29 CDCA ethyl ester was described as an intermediate in the synthesis of chenodiol by reduction of (5β,7α)-7-hydroxy-3-oxocholan-24-oic acid ethyl ester.…”
Section: Enzymatic Esterificationmentioning
confidence: 99%
“…23 At the same time XRD and solid-state NMR studies revealed the presence of polymorphism in both substances. PXRD analysis already revealed one of the components being DCA dihydrate, and the other component being unidentified.…”
Section: Methodsmentioning
confidence: 94%
“…While one of the two molecules (molecule a) shows intermolecular hydrogen bonding (Figure 6) between the carboxylic groups, the other (molecule b) forms intermolecular hydrogen bonding between the carboxylic group and 3R-OH group of two different bile acid molecules. It is interesting to note that the mode of hydrogen bonding exhibited by molecule b (Figure 6) is similar to the packing pattern of 7R-O-pentenoyloxy derivative of chenodeoxycholic acid recently reported by Dias et al 23 Along with differences in side chain conformation, differences in the To further support our interpretation differential scanning calorimetry (DSC) studies were carried out. In case of commercial CA 1, the substance is almost completely in highly crystalline anhydrous form as a sharp melting transition, characteristic of CA, can be observed (Figure S4, Supporting Information) at 201.0 °C (lit.…”
mentioning
confidence: 99%
“…Monoester 3 was obtained by the selective removal of the 3R-ethoxycarbonyloxy and 24-ester methyl groups of 2 under mild basic conditions. 8 Cyclodimer 4 was obtained in 80% yield by condensation of two molecules of 3. Large prisms of cyclodimer 4 were obtained by slow evaporation of a chloroformÀacetone solution and proved to be suitable for X-ray analysis.…”
mentioning
confidence: 99%
“…The 4-pentenoate group was introduced at the 7α position of compound 1 under Yamaguchi reaction conditions in high yield (95%) to give triester 2 . Monoester 3 was obtained by the selective removal of the 3α-ethoxycarbonyloxy and 24-ester methyl groups of 2 under mild basic conditions . Cyclodimer 4 was obtained in 80% yield by condensation of two molecules of 3 .…”
mentioning
confidence: 99%