1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-3-O-(4-methoxybenzyl)-sn-glycerol | 888959-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-3-O-(4-methoxybenzyl)-sn-glycerol
• 英文别名: [(2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]propyl] 6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 888959-47-5
• 化学式: C₂₈H₄₉NO₇Si
• 分子量: 539.785
• InChiKey: OABIBYRJXFFSEP-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  37
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-3-O-(4-methoxybenzyl)-sn-glycerol 在 palladium on activated charcoal 四氮唑 、 水 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， -40.0~20.0 ℃ 、344.74 kPa 条件下， 反应 13.5h， 生成 FS-3
  参考文献：
  名称：

  Fluorogenic Phospholipid Substrate to Detect Lysophospholipase D/Autotaxin Activity

  摘要：

  Lysophospholipase D (lysoPLD), also known as autotaxin (ATX), is an important source of the potent mitogen lysophosphatidic acid (LPA). Two fluorogenic substrate analogues for lysoPLD were synthesized in nine steps from (S)-PMB-glycerol. The substrates (FS-2 and FS-3) show significant increases in fluorescence when treated with recombinant ATX and have potential applications in screening for this emerging drug target.

  DOI：

  10.1021/ol060414i
• 作为产物：
  描述：

  (R)-3-(4-methoxybenzyloxy)propane-1,2-diol 在 咪唑 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-O-[6-(N-Boc-amino)hexanoyl]-2-O-tert-butyldimethylsilyl-3-O-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  Fluorogenic Phospholipid Substrate to Detect Lysophospholipase D/Autotaxin Activity

  摘要：

  Lysophospholipase D (lysoPLD), also known as autotaxin (ATX), is an important source of the potent mitogen lysophosphatidic acid (LPA). Two fluorogenic substrate analogues for lysoPLD were synthesized in nine steps from (S)-PMB-glycerol. The substrates (FS-2 and FS-3) show significant increases in fluorescence when treated with recombinant ATX and have potential applications in screening for this emerging drug target.

  DOI：

  10.1021/ol060414i

文献信息

• Fluorogenic Phospholipid Substrate to Detect Lysophospholipase D/Autotaxin Activity
  作者：Colin G. Ferguson、Cleve S. Bigman、Robyn D. Richardson、Laurens A. van Meeteren、Wouter H. Moolenaar、Glenn D. Prestwich

  DOI：10.1021/ol060414i

  日期：2006.5.1

  Lysophospholipase D (lysoPLD), also known as autotaxin (ATX), is an important source of the potent mitogen lysophosphatidic acid (LPA). Two fluorogenic substrate analogues for lysoPLD were synthesized in nine steps from (S)-PMB-glycerol. The substrates (FS-2 and FS-3) show significant increases in fluorescence when treated with recombinant ATX and have potential applications in screening for this emerging drug target.