The syntheses of optically active 3-methylthio hexanol and 3-methylthio hexyl actetate were studied starting from (E)-2-hexenal through reduction, the Sharpless asymmetric epoxidation, regioselective reduction and SN2 nucleophilic substitution. (E)-2-hexenal was reduced by NaBH4 to give (E)-2-hexenol in about 91% yield. The optically active 2, 3-epoxy hexanol was obtained through the Sharpless asymmetric epoxidation of (E)-2-hexenol with about 94% e.e. in about 86% yield. 2, 3-Epoxy hexanol was regioselectively reduced with Red-Al to give optically active 1, 3-hexanediol in about 82% yield. After the primary hydroxy group of 1, 3-hexanediol was transformed to acetate and 3-hydroxy was transformed to mesylate, an SN2 nucleophilic substitution by the reaction with self-made sodium thiomethoxide was carried out to form 3-methylthio hexanol. The overall yield of these three steps was about 59%. 3-Methylthio hexanol was esterified with acetic anhydride to give 3-methylthio hexyl acetate in about 87% yield. The final products 3-methylthio hexanol and 3-methylthio hexyl actate were obtained with about 94% e.e..