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| 1256752-66-5

中文名称
——
中文别名
——
英文名称
——
英文别名
——
化学式
CAS
1256752-66-5
化学式
C22H22Cl3F3N2O8
mdl
——
分子量
605.779
InChiKey
FZRPOQXKYSYTJC-FVVUREQNSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.01
  • 重原子数:
    38.0
  • 可旋转键数:
    7.0
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.5
  • 拓扑面积:
    133.57
  • 氢给体数:
    1.0
  • 氢受体数:
    10.0

反应信息

  • 作为反应物:
    描述:
    (1S,2R,3S,4R,5R,6S)-4,5,6-tris(benzyloxy)-2-hydroxycyclohexane-1,3-diyl diacetate 在 Ni(4-F-PhCN)4Cl2silver trifluoromethanesulfonate 作用下, 以 二氯甲烷 为溶剂, 以94%的产率得到(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-(((1S,2R,3R,4S,5S,6R)-2,6-diacetoxy-3,4,5-tris(benzyloxy)cyclohexyl)oxy)-5-((2-(trifluoromethyl)benzylidene)amino)tetrahydro-2H-pyran-3,4-diyl diacetate
    参考文献:
    名称:
    Nickel-catalyzed α-glycosylation of C(1)-hydroxyld-myo-inositol: a formal synthesis of mycothiol
    摘要:
    mycothiol 的正式合成是通过镍催化 D-myo-肌醇的 C(1)-羟基与 C(2)-N-取代的亚苄基氨基 N-苯基三氟乙酰亚胺酯供体的 α-糖基化来开发的。所获得的假低聚糖具有良好的产率和优异的α选择性。在温和条件下去除C(2)-N-2-三氟甲基苯基-亚苄基基团提供假二糖,完成菌硫醇的正式合成。
    DOI:
    10.1039/c2cc35823a
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文献信息

  • Nickel-Catalyzed Stereoselective Glycosylation with C(2)-<i>N</i>-Substituted Benzylidene <scp>d</scp>-Glucosamine and Galactosamine Trichloroacetimidates for the Formation of 1,2-<i>cis</i>-2-Amino Glycosides. Applications to the Synthesis of Heparin Disaccharides, GPI Anchor Pseudodisaccharides, and α-GalNAc
    作者:Enoch A. Mensah、Fei Yu、Hien M. Nguyen
    DOI:10.1021/ja106682m
    日期:2010.10.13
    α-selectivity. The reactive sites of the nucleophiles or the nature of the protecting groups have little effect on the α-selectivity. This methodology has also been successfully applied to both disaccharide donors and acceptors to provide the corresponding oligosaccharides in high yields and α-selectivity. The efficacy of the nickel procedure has been further applied toward the preparation of heparin disaccharides
    1,2-cis-2-amino glycosides 是在各种生物学上重要的寡糖和糖肽中发现的关键成分。尽管 1,2-cis-2-基糖苷的合成取得了显着进展,但目前最先进方法的缺点包括底物范围有限、产率低、反应时间长和异头混合物。我们开发了一种通过催化的 α-选择性糖基化与 C(2)-N-取代的亚苄基 D-葡糖胺和半乳糖胺三酰亚胺合成 1,2-顺-2-基糖苷的新方法。这些糖基供体能够与多种醇偶联,以高产率提供具有出色 α 选择性的糖缀合物。此外,仅需要亚化学计量的 (5-10 mol%) 才能在 25 °C 下进行反应。目前的方法依赖于配体配合物的性质来控制 α 选择性。亲核试剂的反应位点或保护基团的性质对α-选择性几乎没有影响。该方法也已成功应用于二糖供体和受体,以高产率和 α 选择性提供相应的寡糖过程的功效已进一步应用于制备肝素二糖、GPI 锚定假二糖和 α-Glu
  • Studies on the Selectivity Between Nickel-Catalyzed 1,2-<i>cis</i>-2-Amino Glycosylation of Hydroxyl Groups of Thioglycoside Acceptors with C(2)-Substituted Benzylidene <i>N</i>-Phenyl Trifluoroacetimidates and Intermolecular Aglycon Transfer of the Sulfide Group
    作者:Fei Yu、Hien M. Nguyen
    DOI:10.1021/jo301050q
    日期:2012.9.7
    glycoconjugates bearing the 1,2-cis-2-amino glycosidic linkages because the saccharide thioglycosides obtained can serve as donors for another coupling iteration. This approach streamlines selective deprotection and anomeric derivatization steps prior to the subsequent coupling event. We have developed an efficient approach for the synthesis of highly yielding and α-selective saccharide thioglycosides containing
    包含 1,2-顺式-2-基糖苷键的糖糖苷的立体选择性合成具有挑战性。除了在 1,2-顺式-2-基糖苷键形成中实现高α-选择性的困难之外,糖基化反应还受到异头硫化物基团从糖基受体到糖基供体的不希望的转移的阻碍。克服这些障碍将为制备带有 1,2-顺式分子的寡糖和糖缀合物铺平道路。-2-基糖苷键,因为获得的糖糖苷可以作为另一次偶联迭代的供体。这种方法在随后的偶联事件之前简化了选择性去保护和异头衍生化步骤。我们开发了一种有效的方法来合成含有 1,2-顺式-2-基糖苷键的高产率和 α-选择性糖糖苷,通过阳离子催化的带有 2-三甲基苯基苷元的糖苷受体的糖基化与N-苯基三酰亚胺酯供体。2-三甲基苯基有效地阻止异头硫化物基团从糖基受体转移到 C(2)-亚苄基供体,并且易于安装和激活。目前的方法还突出了催化剂在糖基受体上存在异头硫化物基团的情况下选择性活化 C(2)-亚苄基亚胺酯基团的功效。
  • Stereoselective α-glycosylation of C(6)-hydroxyl myo-inositols via nickel catalysis—application to the synthesis of GPI anchor pseudo-oligosaccharides
    作者:Matthew S. McConnell、Enoch A. Mensah、Hien M. Nguyen
    DOI:10.1016/j.carres.2013.09.006
    日期:2013.11
    Glycosylphosphatidyl inositol (GPI) anchors play a key role in many eukaryotic biological pathways. Stereoselective synthesis of GPI anchor analogues have proven to be critical for probing the biosynthesis, structure, and biological properties of these compounds. Challenges that have emerged from these efforts include the preparation of the selectively protected myo-inositol building blocks and the stereoselective construction of glucosamine alpha-linked myo-inositol containing pseudodisaccharide units. Herein, we describe the effectiveness of the cationic nickel(II) catalyst, Ni(4-F-PhCN)(4)(OTf)(2), at promoting selective formation of 1,2-cis-2-amino glycosidic bonds between the C(2)-N-substituted benzylideneamino trihaloacetimidate donors and C(6)-hydroxyl myo-inositol acceptors. This catalytic coupling process allows rapid access to pseudosaccharides of GPI anchors in good yields and with excellent levels of a-selectivity (alpha:beta = 10:1-20:1). In stark contrast, activation of trichloroacetimidate donors containing the C(2)-N-substituted benzylidene group with TMSOTf and BF3.OEt2 provided the desired pseudodisaccharides as a 1: 1 mixture of alpha- and beta-isomers. (C) 2013 Elsevier Ltd. All rights reserved.
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