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The title compound, C 27 H 30 O 6 , was prepared by monodihydroxy­lation of the bis-olefin ( E , E )- tert -butyl 2-acetyl-2-cinnamyl-5-phenyl­pent-4-enoate using standard Sharpless asymmetric dihydroxy­lation conditions, followed by treatment with 1,1′-carbonyl diimidazole. In the crystal structure, the phenyl rings form an intra­molecular edge-to-face C—H⋯π contact with an inter­planar angle of 56.4° and a H⋯centroid distance of 3.03 Å.

(2S,4′R,5′R)-(E)-tert-Butyl 2-acetyl-2-(2-oxo-5-phenyl-1,3-dioxolan-4-ylmethyl)-5-phenylpent-4-enoate