Facile Stereoselective Syntheses of Four of the Six 1, 2, 3, 4-Cyclohexanetetrols: Increasing the Accessibility of Cyclitols for Probing the Molecular Recognition of Saccharides

Abstract

New and stereoselective syntheses of (1,2,3/4)-, (1,2/3,4)-, (1,4/2,3)-, and (1,2,4/3)-cyclohexanetetrols (1, 2, 3, and 4 respectively) are described. The known syn and anti 1,4-cyclohex-2-enediols 9 and 10 were used as starting materials. Diols 9 and 10 were allow to react with OsO₄ to directly form 3 and 1 respectively. Diols 9 and 10 were epoxidized with MCPBA, which yielded 4 and 2 after acid catalyzed epoxide opening.