sodium 3′,4,4′-tri-O-benzyl-2,3,6,6′-tetra-O-palmitoyl-2′-O-sulfate-α,α-D-trehalose | 1448242-71-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: sodium 3′,4,4′-tri-O-benzyl-2,3,6,6′-tetra-O-palmitoyl-2′-O-sulfate-α,α-D-trehalose
• 英文别名: sodium;[(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-3,4-di(hexadecanoyloxy)-6-(hexadecanoyloxymethyl)-5-phenylmethoxyoxan-2-yl]oxy-6-(hexadecanoyloxymethyl)-4,5-bis(phenylmethoxy)oxan-3-yl] sulfate
• CAS: 1448242-71-4
• 化学式: C₉₇H₁₅₉O₁₈S*Na
• 分子量: 1668.37
• InChiKey: XTVNQOVNUDWJCZ-SXYCHFRYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  21.89
• 重原子数：
  117
• 可旋转键数：
  79
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  sodium 3′,4,4′-tri-O-benzyl-2,3,6,6′-tetra-O-palmitoyl-2′-O-sulfate-α,α-D-trehalose 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到sodium 2,3,6,6′-tetra-O-palmitoyl-2′-O-sulfate-α,α-D-trehalose
  参考文献：
  名称：

  Synthesis of a Mycobacterium tuberculosis Tetra-acylated Sulfolipid Analogue and Characterization of the Chiral Acyl Chains Using Anisotropic NAD 2D-NMR Spectroscopy

  摘要：

  Tetra-O-acylated sulfolipids are metabolites found in the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Their role in pathogenesis remains, however, undefined. Here we describe a novel access to model tetra-O-acylated trehalose sulfate derivatives having simple acyl chains. The trehalose core was regioselectively protected using a tandem procedure with catalytic iron(III) chloride hexahydrate and further desymmetrized. Model chiral fatty acids, prepared by a zinc-mediated cross-coupling, were incorporated into the trehalose core. The enantiomeric excess of the chiral fatty acids has been measured by natural abundance deuterium (NAD) 2D-NMR spectroscopy in a polypeptide based chiral liquid crystal. The synthetic approach established for the model compounds can easily be developed for the preparation of other analogues and natural sulfolipids.

  DOI：

  10.1021/jo4012255
• 作为产物：
  描述：

  3′,4,4′-tri-O-benzyl-2,3,6,6′-tetra-O-palmitoyl-α,α-D-trehalose 在 吡啶 、 三氧化硫吡啶 作用下， 反应 3.0h， 以96%的产率得到sodium 3′,4,4′-tri-O-benzyl-2,3,6,6′-tetra-O-palmitoyl-2′-O-sulfate-α,α-D-trehalose
  参考文献：
  名称：

  Synthesis of a Mycobacterium tuberculosis Tetra-acylated Sulfolipid Analogue and Characterization of the Chiral Acyl Chains Using Anisotropic NAD 2D-NMR Spectroscopy

  摘要：

  Tetra-O-acylated sulfolipids are metabolites found in the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Their role in pathogenesis remains, however, undefined. Here we describe a novel access to model tetra-O-acylated trehalose sulfate derivatives having simple acyl chains. The trehalose core was regioselectively protected using a tandem procedure with catalytic iron(III) chloride hexahydrate and further desymmetrized. Model chiral fatty acids, prepared by a zinc-mediated cross-coupling, were incorporated into the trehalose core. The enantiomeric excess of the chiral fatty acids has been measured by natural abundance deuterium (NAD) 2D-NMR spectroscopy in a polypeptide based chiral liquid crystal. The synthetic approach established for the model compounds can easily be developed for the preparation of other analogues and natural sulfolipids.

  DOI：

  10.1021/jo4012255

文献信息

• Synthesis of a <i>Mycobacterium tuberculosis</i> Tetra-acylated Sulfolipid Analogue and Characterization of the Chiral Acyl Chains Using Anisotropic NAD 2D-NMR Spectroscopy
  作者：Aurélie Lemétais、Yann Bourdreux、Philippe Lesot、Jonathan Farjon、Jean-Marie Beau

  DOI：10.1021/jo4012255

  日期：2013.8.2

  Tetra-O-acylated sulfolipids are metabolites found in the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Their role in pathogenesis remains, however, undefined. Here we describe a novel access to model tetra-O-acylated trehalose sulfate derivatives having simple acyl chains. The trehalose core was regioselectively protected using a tandem procedure with catalytic iron(III) chloride hexahydrate and further desymmetrized. Model chiral fatty acids, prepared by a zinc-mediated cross-coupling, were incorporated into the trehalose core. The enantiomeric excess of the chiral fatty acids has been measured by natural abundance deuterium (NAD) 2D-NMR spectroscopy in a polypeptide based chiral liquid crystal. The synthetic approach established for the model compounds can easily be developed for the preparation of other analogues and natural sulfolipids.