STEREOCHEMICAL STUDIES: III. REACTIONS OF 4-OXA-5α-CHOLESTAN-3α-OL, A CARBOHYDRATE MODEL
- 1 October 1961
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 39 (10), 2069-2085
- https://doi.org/10.1139/v61-276
Abstract
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.Keywords
This publication has 6 references indexed in Scilit:
- Racemic 2-Hydroxymethyl-2,3-dihydro-4H-pyran, a Model Carbohydrate1The Journal of Organic Chemistry, 1958
- Ring-Chain Tautomerism of Hydroxy AldehydesJournal of the American Chemical Society, 1952
- The hydration of acetaldehyde in aqueous solutionTransactions of the Faraday Society, 1952
- Hydroxylation of 2,3-Dihydropyran and the Application of Desoxyaldopentoses in the Browning Reaction1Journal of the American Chemical Society, 1948
- Preparation of Dihydropyran, δ-Hydroxyvaleraldehyde and 1,5-Pentanediol from Tetrahydrofurfuryl AlcoholJournal of the American Chemical Society, 1946
- The Reduction of Aldoses at the Dropping Mercury Cathode: Estimation of the aldehydo Structure in Aqueous Solutions1Journal of the American Chemical Society, 1940