Synthesis of α-C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-epi-C-Glycoside of KRN7000

Ya Jen Chang, Yi Chen Hsuan, Alan Chuan Ying Lai, Yun Chiann Han, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

A new immunostimulant, the 4′-epimer of α-C-GalCer, was synthesized from a C2-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 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)808-811
Number of pages4
JournalOrganic Letters
Volume18
Issue number4
DOIs
StatePublished - 19 Feb 2016

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