1 research outputs found
Synthesis of α‑C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-<i>epi</i>-C-Glycoside of KRN7000
A new immunostimulant,
the 4′-epimer of α-C-GalCer,
was synthesized from a <i>C</i><sub>2</sub>-symmetric dienediol
and α-C-allyl galactoside. The intramolecular aziridination
and the following reductive ring opening provided the core of the
aliphatic amino alcohol with excellent regio- and stereocontrol. The
new immunostimulants <b>3d</b> and <b>3e</b> gave a better
polarized Th1-type cytokine response in murine NKT cells than the
benchmarked α-C-GalCer