From D-xylose to a D-glycero-L-altrose derivative

被引:1
作者
Banchet-Cadeddu, Aline [1 ]
Haudrechy, Arnaud [1 ]
机构
[1] Univ Reims, UMR CNRS 7312, Inst Chim Mol Reims, F-51687 Reims, France
关键词
D-Glycero-L-altrose; D-Xylose; KRN; 7000; Dihydroxylation; KILLER T-CELLS; NONOBESE DIABETIC MICE; ALPHA-GALACTOSYLCERAMIDE PREVENTS; CD1D-RESTRICTED NKT CELLS; HIGHER-CARBON SUGARS; PANAX-GINSENG; HEPATIC METASTASIS; CARBOXYLIC-ACIDS; DIASTEREOMERS; C-GLYCOSIDES;
D O I
10.1016/j.tetlet.2014.06.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A key intermediate corresponding to a rare sugar framework has been synthesized, starting from D-xylose, an inexpensive carbohydrate. This approach gave access to new elaborated sugar moieties for structure-activity relationships in the KRN research. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4605 / 4607
页数:3
相关论文
共 72 条
  • [1] Reactivity of glucosyl radical in the presence of phenols
    Alberti, A
    DellaBona, MA
    Macciantelli, D
    Pelizzoni, F
    Sello, G
    Torri, G
    Vismara, E
    [J]. TETRAHEDRON, 1996, 52 (30) : 10241 - 10248
  • [2] Acetobromomaltose, a new source of carbohydrate radicals.: EPR characterisation of maltosyl and 2-deoxymaltos-2-yl radicals and syntheses of tetrasaccharide-like mimics, maltal, 3-α-maltosyl propiononitrile, 1,5-anhydromaltitol and 2-deoxymaltopyranoside
    Alberti, A
    Bertini, S
    Comoli, M
    Guerrini, M
    Mele, A
    Vismara, E
    [J]. TETRAHEDRON, 2000, 56 (34) : 6291 - 6297
  • [3] The stimulating adventure of KRN 7000
    Banchet-Cadeddu, Aline
    Henon, Eric
    Dauchez, Manuel
    Renault, Jean-Hugues
    Monneaux, Fanny
    Haudrechy, Arnaud
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (09) : 3080 - 3104
  • [4] DEOXY-NITROSUGARS .6. STEREOELECTRONIC CONTROL IN THE REDUCTIVE DENITRATION OF TERTIARY NITRO ETHERS - A SYNTHESIS OF C-GLYCOSIDES
    BAUMBERGER, F
    VASELLA, A
    [J]. HELVETICA CHIMICA ACTA, 1983, 66 (07) : 2210 - 2222
  • [5] ALDOLASE-CATALYZED SYNTHESIS OF COMPLEX C-8 AND C-9 MONOSACCHARIDES
    BEDNARSKI, MD
    WALDMANN, HJ
    WHITESIDES, GM
    [J]. TETRAHEDRON LETTERS, 1986, 27 (48) : 5807 - 5810
  • [6] Hypothesized role of galactocerebroside and NKT cells in the etiology of multiple sclerosis
    Blewett, Megan M.
    [J]. MEDICAL HYPOTHESES, 2008, 70 (04) : 826 - 830
  • [7] HIGHER-CARBON SUGARS .15. DOUBLE ASYMMETRIC INDUCTION IN THE CATALYTIC OSMYLATION OF SOME ALPHA,BETA-UNSATURATED OCTURONIC ACID-DERIVATIVES
    BRIMACOMBE, JS
    MCDONALD, G
    RAHMAN, MA
    [J]. CARBOHYDRATE RESEARCH, 1990, 205 : 422 - 427
  • [8] Potent immune-modulating and anticancer effects of NKT cell stimulatory glycolipids
    Chang, Ya-Jen
    Huang, Jing-Rong
    Tsai, Yi-Chien
    Hung, Jung-Tung
    Wu, Douglass
    Fujio, Masakazu
    Wong, Chi-Huey
    Yu, Alice L.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (25) : 10299 - 10304
  • [9] Synthesis of long-chain monosaccharides via the coupling of three 'normal' sugar units via Wittig type methodology: unusual removal of the benzyl group under basic conditions
    Cieplak, Maciej
    Jarosz, Slawomir
    [J]. TETRAHEDRON-ASYMMETRY, 2011, 22 (18-19) : 1757 - 1762
  • [10] Increased susceptibility to tumor initiation and metastasis in TNF-related apoptosis-inducing ligand-deficient mice
    Cretney, E
    Takeda, K
    Yagita, H
    Glaccum, M
    Peschon, JJ
    Smyth, MJ
    [J]. JOURNAL OF IMMUNOLOGY, 2002, 168 (03) : 1356 - 1361