(R)-10-methyloctadecan-1-ol | 883878-56-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-10-methyloctadecan-1-ol
• 英文别名: (10R)-10-methyloctadecan-1-ol
• CAS: 883878-56-6
• 化学式: C₁₉H₄₀O
• 分子量: 284.526
• InChiKey: FJQSPAMDIRQNCS-LJQANCHMSA-N

物化性质

• 沸点：
  344.8±10.0 °C(Predicted)
• 密度：
  0.836±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-10-methyloctadecan-1-ol 在 4-二甲氨基吡啶 、 potassium permanganate 、 四丁基溴化铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 3-O-benzyl-2-O-((R)-10-methyloctadecanoyl)-1-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599
• 作为产物：
  描述：

  magnesium,hexoxymethylbenzene,bromide 在 吡啶 、 aluminum oxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 177.0h， 生成 (R)-10-methyloctadecan-1-ol
  参考文献：
  名称：

  Synthesis and Structure of Phosphatidylinositol Dimannoside

  摘要：

  (R)-Tuberculostearic acid (2) was synthesized in seven steps from (S)-citronellol (5). The carbon chain of 2 was assembled by copper-catalyzed cross coupling of (S)-citronellol tosylate (6) and hexylmagnesium bromide; subsequent ozonolysis and reaction with 6-benzyloxyhexylmagnesium bromide furnished alcohol 10. Functional group manipulation afforded (R)-2 in 49% overall yield from 5. DCC coupling of (R)-2 with 3-O-benzyl-1-O-palmitoyl-sn-glycerol (16), followed by hydrogenolytic removal of the benzyl group and treatment with benzyl bis(diisopropyl)phosphoramidite, afforded phosphoramidite 20. Tetrazole-mediated coupling of 20 with PIM1 head group 21 gave 22, and subsequent debenzylation afforded phosphatidylinositol mono-mannoside, PIM1 (23). Similarly, coupling of 20 and 24 and removal of the benzyl protecting groups gave PIM2 (1c). Both 23 and 1c have a clearly defined acylation pattern, which was confirmed by mass spectrometry, with sn-1 palmitoyl and sn-2 tuberculostearoyl groups on the glycerol moiety. Both 23 and 1c were shown to modulate the release of the pro-inflammatory cytokine, IL-12, in a dendritic cell assay.

  DOI：

  10.1021/jo0625599

文献信息

• Total Synthesis of Phosphatidylinositol Mannosides of <i>Mycobacterium tuberculosis</i>
  作者：Xinyu Liu、Bridget L. Stocker、Peter H. Seeberger

  DOI：10.1021/ja0565368

  日期：2006.3.1

  The total synthesis of phosphatidylinositol mannosides (PIMs), a key class of antigenic glycolipids found on the cell wall of Mycobacterium tuberculosis, is described. The synthetic strategy relied on a [4 + 3] glycosylation of tetramannoside 1 and pseudotrisaccharide 2, which allowed for convergent access to the glycan backbone of the phosphatidylinositol dimannoside (PIM2) and hexamannoside (PIM6)

  描述了磷脂酰肌醇甘露糖苷 (PIM) 的全合成，这是在结核分枝杆菌细胞壁上发现的一类关键抗原糖脂。合成策略依赖于四甘露糖苷 1 和假三糖 2 的 [4 + 3] 糖基化，这允许聚合访问磷脂酰肌醇二甘露糖苷 (PIM2) 和六甘露糖苷 (PIM6) 的聚糖骨架。基于铜催化的交叉偶联反应实现了结核硬脂酸的简短实用合成。聚糖和脂质部分的结合导致了天然 PIM2 和 PIM6 的首次全合成。