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

doi:10.1021/acs.orglett.6b00090

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

化學學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

26 引文斯高帕斯（Scopus）

摘要

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).

原文	???core.languages.en_GB???
頁（從 - 到）	808-811
頁數	4
期刊	Organic Letters
卷	18
發行號	4
DOIs	https://doi.org/10.1021/acs.orglett.6b00090
出版狀態	已出版 - 19 2月 2016

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10.1021/acs.orglett.6b00090

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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).",

author = "Chang, {Ya Jen} and Hsuan, {Yi Chen} and Lai, {Alan Chuan Ying} and Han, {Yun Chiann} and Hou, {Duen Ren}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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T2 - The New Immunostimulant 4′-epi-C-Glycoside of KRN7000

AU - Chang, Ya Jen

AU - Hsuan, Yi Chen

AU - Lai, Alan Chuan Ying

AU - Han, Yun Chiann

AU - Hou, Duen Ren

PY - 2016/2/19

Y1 - 2016/2/19

N2 - 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).

AB - 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).

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DO - 10.1021/acs.orglett.6b00090

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JO - Organic Letters

JF - Organic Letters

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

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