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-2-O-sulfate sodium salt | 1007886-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 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-2-O-sulfate sodium salt
• 英文别名: sodium;[(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-3-hexadecanoyloxy-6-[[(2S)-2-methylicosanoyl]oxymethyl]-4-[(2S)-2-methyloctadecanoyl]oxy-5-phenylmethoxyoxan-2-yl]oxy-6-[[(2S)-2-methylicosanoyl]oxymethyl]-4,5-bis(phenylmethoxy)oxan-3-yl] sulfate
• CAS: 1007886-01-2
• 化学式: C₁₁₀H₁₈₅O₁₈S*Na
• 分子量: 1850.72
• InChiKey: UXVQETIXRFELSA-DASUDZFPSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  26.53
• 重原子数：
  130
• 可旋转键数：
  89
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  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-2-O-sulfate sodium salt 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以53%的产率得到6,6'-di-O-((S)-2-methylarachidoyl)-3'-O-((S)-2-methylstearoyl)-2'-O-palmitoyl-α,α-D-trehalose-2-O-sulfate sodium salt
  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