3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-2,3-di-O-palmitoyl-α,α-D-trehalose | 1448242-64-5

• 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: 3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-2,3-di-O-palmitoyl-α,α-D-trehalose
• 英文别名: [(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-3-hexadecanoyloxy-6-(hydroxymethyl)-5-phenylmethoxyoxan-4-yl] hexadecanoate
• CAS: 1448242-64-5
• 化学式: C₇₁H₁₁₄O₁₃Si
• 分子量: 1203.76
• InChiKey: PCTATEWDZNZWQP-UWPFXCCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.37
• 重原子数：
  85
• 可旋转键数：
  48
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-2,3-di-O-palmitoyl-α,α-D-trehalose 、 棕榈酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-2,3,6,6′-tetra-O-palmitoyl-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′-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-2,3-di-O-palmitoyl-α,α-D-trehalose 在 三乙基硅烷 、 二氯苯酚溴酯 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以93%的产率得到3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-2,3-di-O-palmitoyl-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.