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

被引：22

作者：

Chang, Ya-Jen ^{[2
]}

Hsuan, Yi-Chen ^{[1
]}

Lai, Alan Chuan-Ying ^{[2
]}

Han, Yun-Chiann ^{[2
]}

Hou, Duen-Ren ^{[1
]}

机构：

[1] Natl Cent Univ, Dept Chem, 300 Jhong Da Rd, Taoyuan 32001, Taiwan

[2] Acad Sinica, Inst Biomed Sci, 128 Acad Rd,Sect 2, Taipei 11529, Taiwan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 04期

关键词：

KILLER T-CELLS; OLEFIN CROSS-METATHESIS; SPONGE AGELAS-MAURITIANUS; VICINAL AMINO-ALCOHOLS; GLYCOSIDE ANALOG; RECOGNITION; LIGAND; GLYCOSPHINGOLIPIDS; STEREOCHEMISTRY; OXAZOLIDINONES;

D O I：

10.1021/acs.orglett.6b00090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new immunostimulant, the 4'-epimer of alpha-C-GalCer, was synthesized from a C-2-syminetric dienediol arid alpha-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 alpha-C-GalCer.

引用

页码：808 / 811

页数：4

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