Study Of Synthesizing (S)-3-hydroxybutyrolactone And Its Derivative (S)-1,2,4-butanetriol

(S)-3-hydroxybutyrolactone and its derivative (S)-1,2,4-butanetriol are important building blocks of asymmetric synthesis and key intermediates in the synthesis of Atorvatitatin,L-carnitine, HIV-1 protease amperanavir and other medicines as well, so, studies on their synthesis are of great practical significance. The synthesis of (S)-3-hydroxybutyrolactone and (S)-1,2,4-butanetriol are the major work of this work. The final product is characterized by rotation, HNMR and IR which show that resultants are the objective products.(S)-3-hydroxybutyrolactone has been synthesized by decomposing of hexose. And that is good for environment and of promising prospect for application. With sodium hydroxide and hydrogen peroxide being the oxidizer, maltose was oxidized and decomposed into (S)-3,4-dihydroxyl-butyric acid, which was cycled and esterified to obtain s-3-hydroxybutyrolactone. The final product was purified by flash chromatography .(S)-3-hydroxybutyrolactone has been synthesized by the way that L-malilc acid is anhydridised, esterified, and reduced by NaBH4 followed by hydration and cycling into (S)-3-hydroxybutyrolactone. Effects of catalyst, dosage of solvent, addition of raw materials, reaction time and temperature on product yield are studied. The optimum reaction condition in which the yield was up to 79% is determined. The route has advantages of few by-reaction, high yield and easy operation. (S)-1,2,4-butanetriol has been produced using L-malic acid as raw material. Dimetyl-L-malic ester that is product of esterification of L-malic acid and methanol is reduced by NaBH4 and Lithium chloride followed by separation and purification to obtained (S)-1,2,4-butanetriol. (S)-1,2,4-butanetriol was analyzed by HPLC. Results indicated that the purity is 94.67% with the yield up to 68%. Some improvements in separation process has been done in order to increase the product purity, and simplification of the opearation makes the route go forward one step to industrialization. (S)-1,2,4-butanetriol has been synthesized with (S)-3-hydroxybutyrolactone as raw material. Being mother material for the first time, (S)-3-hydroxybutyrolactone is reduced by NaBH4 that was mild and of high reaction selectivity to produce (S)-1,2,4-butanetriol. Effects of addition order and molar ratio of raw materials, reaction time and temperature on product yield are investigated. The better reaction parameters, in which the yield is more than 82%, are determined. The route is one-step, and has advantages of high yield, mild conditions and easy operation, which lays an elementary foundation for inductrial production.