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
收藏
页码：808 / 811
页数：4
相关论文
共 50 条
  • [41] Synthesis of new 4-aroyl-pyrano[c]chromenes via a one-pot, three-component reaction based on aryl glyoxals
    Khodabakhshi, Saeed
    Karami, Bahador
    Eskandari, Khalil
    Farahi, Mahnaz
    TETRAHEDRON LETTERS, 2014, 55 (28) : 3753 - 3755
  • [42] DESIGN AND SYNTHESIS OF A NOVEL EPOXIDE-CONTAINING PYRROLO[2,1-C][1,4]BENZODIAZEPINE (PBD) VIA A NEW CYCLIZATION PROCEDURE
    WILSON, SC
    HOWARD, PW
    THURSTON, DE
    TETRAHEDRON LETTERS, 1995, 36 (35) : 6333 - 6336
  • [43] Synthesis of new chromeno-annulated cis-fused pyrano[4,3-c]isoxazole derivatives via intramolecular nitrone cycloaddition and their cytotoxicity evaluation
    Bejjanki, Naveen Kumar
    Venkatesham, Akkaladevi
    Madda, Jyothi
    Kommu, Nagaiah
    Pombala, Sujitha
    Kumar, C. Ganesh
    Prasad, Kothakonda Rajendra
    Nanubolu, Jagadeesh Babu
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (14) : 4061 - 4066
  • [44] Facile synthesis of new aromatic cardo polyamides based on 9,9-bis(4-iodophenyl)xanthene via C–N coupling reaction and properties
    Shi-Gao Guo
    Zhi-Hui Huang
    Mei-Hong Wei
    Yong-Jun Liu
    Jing-Wei Zhao
    Shou-Ri Sheng
    Polymer Bulletin, 2023, 80 : 4909 - 4925
  • [45] Facile synthesis of new aromatic cardo polyamides based on 9,9-bis(4-iodophenyl)xanthene via C-N coupling reaction and properties
    Guo, Shi-Gao
    Huang, Zhi-Hui
    Wei, Mei-Hong
    Liu, Yong-Jun
    Zhao, Jing-Wei
    Sheng, Shou-Ri
    POLYMER BULLETIN, 2023, 80 (05) : 4909 - 4925
  • [46] A new strategy to construct a C=C-CF3 subunit via CuBr-catalyzed domino reaction of homopropargyl amines: an efficient synthesis of trifluoromethyl containing building blocks 4-trifluoromethyl-2,3-dihydro-pyrroliums
    Ge, Guang-Cun
    Huang, Xiao-Jun
    Ding, Chang-Hua
    Wan, Shi-Li
    Dai, Li-Xin
    Hou, Xue-Long
    CHEMICAL COMMUNICATIONS, 2014, 50 (23) : 3048 - 3051
  • [47] Entry to new conformationally constrained amino acids.: First synthesis of 3-unsubstituted 4-alkyl-4-carboxy-2-azetidinone derivatives via an intramolecular Nα-Cα-cyclization strategy
    Gerona-Navarro, G
    Bonache, MA
    Herranz, R
    García-López, MT
    González-Muñiz, R
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10): : 3538 - 3547
  • [48] Synthesis of New Imidazolidin-2,4-dione and 2-Thioxo-imidazolidin-4-ones via C-Phenylglycine Derivatives (vol 15, pg 128, 2010)
    de Sousa Luis, Jose Alixandre
    Barbosa Filho, Jose Maria
    Lira, Bruno Freitas
    Medeiros, Isac Almeida
    Soares Lima de Morais, Liana Clebia
    dos Anjos, Raline Mendonca
    dos Santos, Alexsandro Fernandes
    de Oliveira, Cledualdo Soares
    de Athayde-Filho, Petronio Filgueiras
    MOLECULES, 2010, 15 (03) : 1985 - 1986
  • [49] Synthesis of Li2FeSiO4/C Composite as Cathode Materials for Lithium Ion Battery via a New Citric Acid-Assisted Sol-Gel Process
    Huang, Xiaobing
    Ren, Jie
    Wang, Hao
    Peng, Peitian
    Feng, Shiqiang
    Zeng, Xianguang
    Zhou, Shibiao
    Chen, Yuandao
    Liu, Beiping
    INTERNATIONAL JOURNAL OF ELECTROCHEMICAL SCIENCE, 2014, 9 (11): : 6551 - 6557
  • [50] A facile synthesis of new pyrazolo- and triazolo[5,1-c] [1,2,4]triazepine derivatives via intermolecular Wittig ring-closure reaction
    Barsy, MA
    Elrady, EA
    Hassan, ME
    El Latif, FMA
    HETEROCYCLIC COMMUNICATIONS, 2000, 6 (06) : 545 - 551
12345