64986-86-3Relevant articles and documents
Synthesis and spectroscopic studies of new bile acid derivatives linked by a 1,2,3-triazole ring
Pospieszny, Tomasz,Ma?ecka, Izabela,Paryzek, Zdzis?aw
supporting information; experimental part, p. 301 - 305 (2012/02/02)
A novel method for the synthesis of cholic acid derivatives has been developed using 'click chemistry'. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester and azide groups of 3α-azidoacetoxy-7α, 12α-diformyloxy-5β-cholan-24-oate gave a new dimer and oligomer linked by a 1,2,3-triazole ring. The structures of the products were confirmed by spectral (1H NMR, 13C NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASSs).
IMPROVED SYNTHESIS OF 3-KETO, 4-ENE-3-KETO, AND 4,6-DIENE-3-KETO BILE ACIDS
Leppik, Raymond A.
, p. 475 - 484 (2007/10/02)
Cholic and deoxycholic acids can be converted into 3-keto derivatives in 75-80percent yield, by a four-step synthesis consisting of formylation, selective deformylation of the 3-formoxyl group, oxidation, then deformylation of the remaining formoxyl groups.The intermediate 3-keto formoxyl acids in this sequence were shown to be suitable starting compounds for the synthesis of 4-ene-3-keto acids, in 55-60percent yield, via bromination, dehydrobromination, and deformylation.By extending the dehydrobromination reaction, the 7α-formoxyl group of the intermediate 4-ene-3-keto-7α,12α-diformoxyl acid is also lost, hence providing a useful synthetic route to 4,6-diene-3-keto bile acids.
