Efficient synthesis of (3R,5S)-3,5,6-trihydroxyhexanoic acid derivative as a chiral side chain of statins.

[摘要]：Efficient synthesis of (3R,5S)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (I) was accomplished. Unprecedented hydration of (S)-4-hydroxyfuran-2-ylideneacetate in the presence of LiCl provided (R)-5,6-dihydroxy-3-oxohexanoate, the primary OH group of which reacted with pivaloyl- and 1-naphthoyl chloride in pyridine to give the corresponding ester with improved selectivity. Subsequent diastereoselective redn. and protection-deprotection provided I.

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