Use of a Grignard reagent to lengthen a triose carbon chain

Author:

Walton D. J.

Abstract

The addition of vinylmagnesium chloride to 2,3-O-isopropylidene-d-glyceraldehyde (I) gave a mixture of the epimeric pentene derivatives II and V, which were separated by preparative gas–liquid chromatography. Ozonolysis and subsequent deketalization of the individual epimers gave d-threose and d-erythrose, respectively, in yields of ca. 40%. This represents a method of lengthening an aldose carbon chain by one carbon atom.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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