444183-73-7Relevant academic research and scientific papers
Synthesis of 2-methyl-D-erythritol via epoxy ester-orthoester rearrangement
Giner, Jose-Luis,Ferris Jr., William V.,Mullins, Joseph J.
, p. 4856 - 4859 (2002)
The biomimetic epoxy ester-orthoester rearrangement has been applied to a new synthesis of 2-methyl-D-erythritol, a branched five-carbon sugar of importance to the deoxyxylulose pathway of isoprenoid biosynthesis. The intermediate orthoacetate is one of the few [2.2.1]-orthoesters to have been reported. Labeling studies with O-18 indicated that this reaction proceeds exclusively via a 5-exo cyclization. NMR analysis of chiral esters indicated an ee of 87% for the starting epoxide and an ee of 86% for the product. This route represents a rapid and convenient method for the synthesis of 2-methyl-D-erythritol and is expected to be useful for generating isotopically labeled intermediates for biochemical studies.
