325700-26-3Relevant academic research and scientific papers
Synthesis of D- and L-Deoxymannojirimycin via an Asymmetric Aminohydroxylation of Vinylfuran
Haukaas, Michael H.,O'Doherty, George A.
, p. 401 - 404 (2007/10/03)
(Equation Presented) The Sharpless catalytic asymmetric aminohydroxylation has been applied to 2-vinylfuran, producing β-hydroxyfurfurylamine 5a with enantioexcess of >86% and 21% yield from furfural. The Cbz and TBS protected amino alcohol 5a was converted into both the D- and L-isomers of deoxymannojirimycin (DMJ) and deoxygulonojirimycin in five to seven steps and 48% and 66% overall yields. The key steps include the use of an aza-Achmatowicz reaction, a diastereoselective Luche reduction, diastereoselective dihydroxylation, and a tandem Cbz deprotection/reductive amination.
