- Synthesis of [25, 26, 26, 26, 27, 27, 27-d7]-cholesterol
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An efficient synthesis of [25, 26, 26, 26, 27, 27,27-d7]-cholesterol 1, a useful tool for the measurement of cholesterol absorption, is described. Commercially available stigmasterol is converted into the known aldehyde 2 which was then transformed to the d7-cholesterol 1 through a reaction sequence of 8 steps in an overall yield of 22.5%. Copyright
- Chu, Guo-Hua,Li, Pui-Kai
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- Synthesis of cholesterol analogs having varying length alkyl side chains including cholesterol-23, 23, 24, 24, 25, 26, 26, 26, 27, 27, 27-d11 as probes of cholesterol's functions and properties
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Cholesterol-23, 23, 24, 24, 25, 26, 26, 26, 27, 27, 27-d11 and nondeuterated long-chain analogs of cholesterol were prepared by alkylation of cyano-containing sterols with isopentyl-d11 4-methylbenzenesulfonate (1.0 equiv.) or with isoalkyl bromides, followed by reductive decyanation with excess potassium metal and a crown ether in toluene. The products are potentially useful probes of the role of the side-chain of cholesterol in the sterol's interactions with membrane lipids and proteins.
- Baek, Dong Jae,Bittman, Robert
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