3,4,4'-tri-O-benzyl-6,6'-di-O-((S)-2-methylarachidoyl)-3'-O-((S)-2-methylstearoyl)-2'-O-palmitoyl-α,α-D-trehalose | 1007886-00-1

• 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-6,6'-di-O-((S)-2-methylarachidoyl)-3'-O-((S)-2-methylstearoyl)-2'-O-palmitoyl-α,α-D-trehalose
• 英文别名: [(2R,3R,4R,5R,6R)-6-[(2R,3R,4S,5R,6R)-3-hexadecanoyloxy-6-[[(2S)-2-methylicosanoyl]oxymethyl]-4-[(2S)-2-methyloctadecanoyl]oxy-5-phenylmethoxyoxan-2-yl]oxy-5-hydroxy-3,4-bis(phenylmethoxy)oxan-2-yl]methyl (2S)-2-methylicosanoate
• CAS: 1007886-00-1
• 化学式: C₁₁₀H₁₈₆O₁₅
• 分子量: 1748.68
• InChiKey: SKOREDHLBHFMRY-JYOSAOMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  39.5
• 重原子数：
  125
• 可旋转键数：
  87
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  181
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  3,4,4'-tri-O-benzyl-6,6'-di-O-((S)-2-methylarachidoyl)-3'-O-((S)-2-methylstearoyl)-2'-O-palmitoyl-α,α-D-trehalose 在 pyridine-SO3 complex 作用下， 反应 10.0h， 生成 [(2R,3R,4S,5R,6R)-5-hexadecanoyloxy-6-[(2R,3R,4S,5R,6R)-6-[[(2S)-2-methylicosanoyl]oxymethyl]-4,5-bis(phenylmethoxy)-3-sulfooxyoxan-2-yl]oxy-4-[(2S)-2-methyloctadecanoyl]oxy-3-phenylmethoxyoxan-2-yl]methyl (2S)-2-methylicosanoate
  参考文献：
  名称：

  Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

  摘要：

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

  DOI：

  10.1021/jo702032c
• 作为产物：
  描述：

  3,4,4'-tri-O-benzyl-2-O-(p-methoxybenzyl)-6,6'-di-O-((S)-2-methylarachidoyl)-3'-O-((S)-2-methylstearoyl)-2'-O-palmitoyl-α,α-D-trehalose 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 以58%的产率得到3,4,4'-tri-O-benzyl-6,6'-di-O-((S)-2-methylarachidoyl)-3'-O-((S)-2-methylstearoyl)-2'-O-palmitoyl-α,α-D-trehalose
  参考文献：
  名称：

  Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

  摘要：

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

  DOI：

  10.1021/jo702032c

文献信息

• Synthetic Studies toward <i>Mycobacterium tuberculosis</i> Sulfolipid-I
  作者：Clifton D. Leigh、Carolyn R. Bertozzi

  DOI：10.1021/jo702032c

  日期：2008.2.1

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.