Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000

被引：26
|
作者：
Chaulagain, MR
Postema, MHD [1 ]
Valeriote, F
Pietraszkewicz, H
机构：
[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
[2] Henry Ford Hlth Syst, Dept Internal Med, Josephine Ford Canc Ctr, Div Hematol & Oncol, Detroit, MI 48202 USA
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 41期
基金：
美国国家科学基金会;
关键词：
C-glycoside; olefin; ring-closing metathesis (RCM); KRN7000; ceramide; immunostimulant; anti-tumor;
D O I：
10.1016/j.tetlet.2004.07.163
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A ring-closing metathesis approach was employed for the synthesis of a beta-C-glycoside analog of the immunostimulant KRN7000. The protected Gglycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the target compound 5. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7791 / 7794
页数：4
相关论文
共 50 条
  • [1] Expedient synthesis of the α-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000)
    Wipf, Peter
    Pierce, Joshua G.
    ORGANIC LETTERS, 2006, 8 (15) : 3375 - 3378
  • [2] The C-glycoside analogue of the immunostimulant α-galactosylceramide (KRN7000):: Synthesis and striking enhancement of activity
    Yang, GL
    Schmieg, J
    Tsuji, M
    Franck, RW
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) : 3818 - 3822
  • [3] Synthesis of a fluorinated C-glycoside of the immunostimulatory glycolipid KRN7000
    Ali, Khaleel
    Altiti, Ahmad
    Mootoo, David
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [4] Intramolecular Nitrogen Delivery for the Synthesis of C-Glycosphingolipids. Application to the C-Glycoside of the Immunostimulant KRN7000
    Altiti, Ahmad S.
    Mootoo, David R.
    ORGANIC LETTERS, 2014, 16 (05) : 1466 - 1469
  • [5] The total synthesis of the c-glycoside analog of KRN7000, a potent alpha galactosyl ceramide.
    Franck, RW
    Yang, GG
    Schmieg, J
    Tsuji, M
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U256 - U256
  • [6] The First Synthesis of a Thioglycoside Analogue of the Immunostimulant KRN7000
    Dere, Ravindra T.
    Zhu, Xiangming
    ORGANIC LETTERS, 2008, 10 (20) : 4641 - 4644
  • [7] Triazole analogue of the immunostimulant α-galactosylceramide (KRN7000):: Synthesis and evaluation
    Kim, Sanghee
    DRUGS OF THE FUTURE, 2007, 32 : 21 - 21
  • [8] Synthesis of α-C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4′-epi-C-Glycoside of KRN7000
    Chang, Ya-Jen
    Hsuan, Yi-Chen
    Lai, Alan Chuan-Ying
    Han, Yun-Chiann
    Hou, Duen-Ren
    ORGANIC LETTERS, 2016, 18 (04) : 808 - 811
  • [9] Synthesis and Immunostimulatory activity of RCAI-56, 61, 105 and 133, the analogs of KRN7000
    Mori, Kenji
    Tashiro, Takuya
    Shigeura, Tomokuni
    Watarai, Hiroshi
    Taniguchi, Masaru
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [10] Synthesis and biological activity of hydroxylated analogues of KRN7000 (α-galactosylceramide)
    Shiozaki, Masao
    Tashiro, Takuya
    Koshino, Hiroyuki
    Shigeura, Tomokuni
    Watarai, Hiroshi
    Taniguchi, Masaru
    Mori, Kenji
    CARBOHYDRATE RESEARCH, 2013, 370 : 46 - 66
12345