A new way to synthesis of (S)-tert-butyl 6-benzyloxy-5-hydroxy-3-oxohexanoate was investigated. The target compound was successfully prepared via several mildly reaction processes by using R-epichlorohydrin, which is an inexpensive and easily available starting material. Through screening the amounts of BF₃•Et₂O and comparing two different synthetic methods, this route becomes more suitable for large-scale preparation for its high yields, mildly reacting-conditions, easily available materials and facilely purification of products.

Key words: R-epichlorohydrin, (S)-1-benzyloxy-2,3-epoxypropane, (R)-3-chloro-1- benzyloxy-2-propanol, (S)-4-benzyloxy-3-hydroxybutanenitrile, (S)-tert-butyl 6-benzyloxy-5-hydroxy-3-oxohexanoate