Isomerization of oxime-ether during synthesis of clarithromycin was written by Liang, Jianhua;Yao, Guowei. And the article was included in Zhongguo Yaowu Huaxue Zazhi in 2005.Application In Synthesis of 1,1-Diisopropoxycyclohexane This article mentions the following:
The synthesis of clarithromycin was improved by studying the etherification of erythromycin A oxime. The competition between kinetic equilibrium and thermodn. equilibrium would alter the original equilibrium existing between E-oxime and Z-oxime in the presence of acid or base. Under acidic conditions Z-oxime should have been converted into E-oxime, but the etherification results suggested that the procedure reversed. Pure E-oxime and the mixture of E-oxime and Z-oxime (> 7.3: 1, E/Z) would give the etherification products with the same ratio of E/Z, which was determined by the etherification conditions of oxime. Solvents and temperature mainly determined the ratio of E/Z of the products, which was higher than 6 in CH3CN and less than 6 in CH2Cl2, and in CH2Cl2 higher than 4 at 30°C and less than 4 at 20°C. Temperature had more influence on the products in CH2Cl2 than those in CH3CN. Reducing the amount of Z-oxime ether in etherification could enhance the yield of clarithromycin, because E-oxime ether derivatives appeared to be more regioselective than the corresponding Z-isomer. In the experiment, the researchers used many compounds, for example, 1,1-Diisopropoxycyclohexane (cas: 1132-95-2Application In Synthesis of 1,1-Diisopropoxycyclohexane).
1,1-Diisopropoxycyclohexane (cas: 1132-95-2) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Application In Synthesis of 1,1-Diisopropoxycyclohexane
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem