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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

27 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 language	English
Pages (from-to)	808-811
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.6b00090
State	Published - 19 Feb 2016

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

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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T1 - Synthesis of α-C-Galactosylceramide via Diastereoselective Aziridination

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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U2 - 10.1021/acs.orglett.6b00090

DO - 10.1021/acs.orglett.6b00090

M3 - 期刊論文

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AN - SCOPUS:84958948559

SN - 1523-7060

VL - 18

SP - 808

EP - 811

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

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

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