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

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• 作者：Ya-Jen Chang ; Yi-Chen Hsuan ; Alan Chuan-Ying Lai ; Yun-Chiann Han ; Duen-Ren Hou
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：18
• 期：4
• 页码：808-811
• 全文大小：367K
• ISSN：1523-7052

文摘

A new immunostimulant, the 4′-epimer of α-C-GalCer, was synthesized from a <i>Ci>₂-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.