1-O-[8-(benzyloxycarbonylamino)octanoyl]-3-O-triethylsilyl-sn-glycerol | 1228359-82-7

• 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-[8-(benzyloxycarbonylamino)octanoyl]-3-O-triethylsilyl-sn-glycerol
• 英文别名: [(2R)-2-hydroxy-3-triethylsilyloxypropyl] 8-(phenylmethoxycarbonylamino)octanoate
• CAS: 1228359-82-7
• 化学式: C₂₅H₄₃NO₆Si
• 分子量: 481.705
• InChiKey: DTVBIHHALIWFTG-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  33
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  辛酸 、 1-O-[8-(benzyloxycarbonylamino)octanoyl]-3-O-triethylsilyl-sn-glycerol 在 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 5.5h， 以80%的产率得到1-O-[8-(benzyloxycarbonylamino)octanoyl]-2-O-octanoyl-3-O-triethylsilyl-sn-glycerol
  参考文献：
  名称：

  Regioselective Approach to Phosphatidylinositol 3,5-Bisphosphates: Syntheses of the Native Phospholipid and Biotinylated Short-Chain Derivative

  摘要：

  A selective bis-silylation of 1D-O-TBDPS-myo-inositol leads to a 1,3,5-trisubstituted inositol, which can be advanced to the headgroup of phosphatidylinositol-3,5-bisphosphate [PI(3,5)P-2]. A mild, regioselective method for construction of the diacylglycerol moiety containing differing fatty acid chains, including the naturally occurring lipids, was developed. Their union in the synthesis of the cell-signaling molecule PI(3,5)P-2 containing the RP-I-stearoyl and sn-2-arachidonoyl groups is described. The methodology was also used to generate dioctanoyl-PI(3,5)P-2 and a previously unreported biotin-PI(3,5)P-2 conjugate, which was coupled to neutravidin beads and used to pull down PI(3.5)P-2-binding proteins from the cytosolic extract of adrenal neurosecretory cells. We report the specific pull-down of the PI(3,5)P-2-binding protein svp1p, a known PI(3,5)P-2 effector involved in membrane t To flick

  DOI：

  10.1021/jo100393c
• 作为产物：
  描述：

  [(2R)-2-prop-1-en-2-yloxy-3-triethylsilyloxypropyl] 8-[[phenylmethoxy(triethylsilyloxy)methylidene]amino]octanoate 在 水 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以296 mg的产率得到1-O-[8-(benzyloxycarbonylamino)octanoyl]-3-O-triethylsilyl-sn-glycerol
  参考文献：
  名称：

  Regioselective Approach to Phosphatidylinositol 3,5-Bisphosphates: Syntheses of the Native Phospholipid and Biotinylated Short-Chain Derivative

  摘要：

  A selective bis-silylation of 1D-O-TBDPS-myo-inositol leads to a 1,3,5-trisubstituted inositol, which can be advanced to the headgroup of phosphatidylinositol-3,5-bisphosphate [PI(3,5)P-2]. A mild, regioselective method for construction of the diacylglycerol moiety containing differing fatty acid chains, including the naturally occurring lipids, was developed. Their union in the synthesis of the cell-signaling molecule PI(3,5)P-2 containing the RP-I-stearoyl and sn-2-arachidonoyl groups is described. The methodology was also used to generate dioctanoyl-PI(3,5)P-2 and a previously unreported biotin-PI(3,5)P-2 conjugate, which was coupled to neutravidin beads and used to pull down PI(3.5)P-2-binding proteins from the cytosolic extract of adrenal neurosecretory cells. We report the specific pull-down of the PI(3,5)P-2-binding protein svp1p, a known PI(3,5)P-2 effector involved in membrane t To flick

  DOI：

  10.1021/jo100393c

文献信息

• Regioselective Approach to Phosphatidylinositol 3,5-Bisphosphates: Syntheses of the Native Phospholipid and Biotinylated Short-Chain Derivative
  作者：Regan J. Anderson、Shona L. Osborne、Frederic A. Meunier、Gavin F. Painter

  DOI：10.1021/jo100393c

  日期：2010.6.4

  A selective bis-silylation of 1D-O-TBDPS-myo-inositol leads to a 1,3,5-trisubstituted inositol, which can be advanced to the headgroup of phosphatidylinositol-3,5-bisphosphate [PI(3,5)P-2]. A mild, regioselective method for construction of the diacylglycerol moiety containing differing fatty acid chains, including the naturally occurring lipids, was developed. Their union in the synthesis of the cell-signaling molecule PI(3,5)P-2 containing the RP-I-stearoyl and sn-2-arachidonoyl groups is described. The methodology was also used to generate dioctanoyl-PI(3,5)P-2 and a previously unreported biotin-PI(3,5)P-2 conjugate, which was coupled to neutravidin beads and used to pull down PI(3.5)P-2-binding proteins from the cytosolic extract of adrenal neurosecretory cells. We report the specific pull-down of the PI(3,5)P-2-binding protein svp1p, a known PI(3,5)P-2 effector involved in membrane t To flick