Synthesis Of (R),(S)-Glyceraldehyde Acetonide And Stereoselectivity Of Its Wittig Reaction

In pharmacal and chemical industry, (R) and (S)-glyceraldehyde acetonide are known to be useful and inexpensive chiral synthons for a number of enantiomerically pure compounds(EPC). (R) -glyceraldehyde acetonide can be obtained by periodate cleavage of 1,2:5,6-di-O-isopropylidene-D-mannitol but (S)-glyceraldehyde acetonide is not easy to prepare. There are a lot of articles about the preparation and application of (R) and (S)-glyceraldebyde acetonide.Wittig reaction is one of the most important reactions to form carbon carbon double bonds. There are several articles about the Wittig reaction of (R) and (S) -glyceraldehyde acetonide and their applications. Howerer, to our knowledge, the stereoslectivity about the Wittig reaction of (R) and (S)-glyceraldehyde acetonide has not been reported systematically.This dissertation includes two parts:Part 1 :We summerise mechanism, activity and so on of the Wittig reaction in the premise, the focus is its stereoselectivity .We also introduce the evolvement of preparation and application of (R) and (S)- glyceraldehyde acetonide.Part 2: We afford a method to prapere (R) -glyceraldehyde acetonide which has the advantages of high yield, inexpensive medium and environmental friendliness. We also find a proper method to prepare (S)-glyceraldehyd acetonid. It is most important that (R) and (S)-glyceraldebyde acetonid as new reagents was applied in Wittig reaction to research the stereoselectivity of its Wittig reaction with three types of Ylide reagents under different conditions and have some conclusions. We also get some new compounds.