3,3′-di-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-α,α-D-trehalose | 1448242-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3′-di-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-α,α-D-trehalose
• 英文别名: (2R,4aR,6R,7R,8R,8aR)-6-[[(2R,4aR,6R,7R,8S,8aR)-7-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 1448242-49-6
• 化学式: C₄₆H₅₆O₁₁Si
• 分子量: 813.03
• InChiKey: IFRCSLNYSDMCCD-GQHPAWPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  58
• 可旋转键数：
  13
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,3′-di-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-α,α-D-trehalose 在 三乙基硅烷 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 二氯苯酚溴酯 、 甲酸铵 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.75h， 生成 3′,4,4′-tri-O-benzyl-2′-O-tert-butyldimethylsilyl-3-O-[(S)-2-methyloctadecanoyl]-2-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：

  海藻糖 在 吡啶 、 2,6-二甲基吡啶 、 三乙基硅烷 、 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 3,3′-di-O-benzyl-4,6;4′,6′-di-O-benzylidene-2′-O-tert-butyldimethylsilyl-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

• Simplified Deoxypropionate Acyl Chains for<i>Mycobacterium tuberculosis</i>Sulfoglycolipid Analogues: Chain Length is Essential for High Antigenicity
  作者：Benjamin Gau、Aurélie Lemétais、Marco Lepore、Luis Fernando Garcia-Alles、Yann Bourdreux、Lucia Mori、Martine Gilleron、Gennaro De Libero、Germain Puzo、Jean-Marie Beau、Jacques Prandi

  DOI：10.1002/cbic.201300482

  日期：2013.12.16

  The longer, the better: Increasing the lengths of the 1,3‐methyl‐branched fatty acyl chain units in mycobacterial diacylated sulfoglycolipid (Acyl2SGL) analogues led to dramatic improvements in their antigenic properties and gave products more potent than the natural antigen Acyl2SGLs.

  越长越好：分枝杆菌二酰基磺化糖脂（酰基2 SGL）类似物中1,3-甲基支链脂肪酰基链单元长度的增加导致其抗原性显着改善，并且产品比天然抗原酰基更有效2个SGL。
• 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.