Chapter 12, Problem 12.75P

Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with $\text{NaOH}$ and ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{SH}$ in an alcohol–water mixture forms Z. Identify the structure of Y and draw a mechanism f or the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.