1-D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-2-O-methyl-myo-inositol 1-(acetoxymethyl octadecyl phosphate) | 827574-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-2-O-methyl-myo-inositol 1-(acetoxymethyl octadecyl phosphate)
• 英文别名: [[(1R,2R,3S,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5-trihydroxy-6-methoxycyclohexyl]oxy-octadecoxy-oxidophosphaniumyl]oxymethyl acetate
• CAS: 827574-38-9
• 化学式: C₃₄H₆₆NO₁₅P
• 分子量: 759.869
• InChiKey: NNQSPFIMGFETNQ-LPVCRUQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  51
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  252
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1-D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-2-O-methyl-myo-inositol 1-(acetoxymethyl octadecyl phosphate) 在 cytosolic esterase 作用下， 生成 [(1R,2R,3S,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5-trihydroxy-6-methoxycyclohexyl] octadecyl phosphate
  参考文献：
  名称：

  Synthesis of a cell-permeable analogue of a glycosylphosphatidylinositol (GPI) intermediate that is toxic to the living bloodstream form of Trypanosoma brucei

  摘要：

  The synthesis of two cell-permeable analogues related to a GPI intermediate is described for studies with living trypano-somes and human (HeLa) cells. One of the analogues is metabolised by the former GPI pathway and is toxic to the parasite Try-panosoma brucei but not to human cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.112
• 作为产物：
  描述：

  triethylammonium n-octadecyl hydrogenphosphonate 在 palladium dihydroxide 氢气 、 三甲基乙酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 20.0 ℃ 、303.98 kPa 条件下， 反应 3.75h， 生成 1-D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-2-O-methyl-myo-inositol 1-(acetoxymethyl octadecyl phosphate)
  参考文献：
  名称：

  Synthesis of a cell-permeable analogue of a glycosylphosphatidylinositol (GPI) intermediate that is toxic to the living bloodstream form of Trypanosoma brucei

  摘要：

  The synthesis of two cell-permeable analogues related to a GPI intermediate is described for studies with living trypano-somes and human (HeLa) cells. One of the analogues is metabolised by the former GPI pathway and is toxic to the parasite Try-panosoma brucei but not to human cells. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.112