4-Oxa-5α-cholestan-3α-ol was prepared by reduction of 4-oxa-5α-cholestan-3-one with lithium aluminum hydride. It showed several typical carbohydrate reactions, such as mutarotation in aqueous tetrahydrofuran and condensation with alcohols in the presence of hydrogen chloride to give 3-alkoxy-4-oxa-5α-cholestanes. These compounds were also prepared by the reaction of alcohols with 3α-chloro-4-oxa-5α-cholestane in the presence of base. Factors governing the proportions of 3α and 3β isomers formed in these reactions are discussed.
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Edward et al. (1961) studied this question.
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