Hexadecanoic acid (R)-2-[((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-(2-cyano-ethoxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester | 183429-89-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: Hexadecanoic acid (R)-2-[((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-(2-cyano-ethoxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester
• CAS: 183429-89-2
• 化学式: C₆₀H₉₈NO₁₅P
• 分子量: 1104.41
• InChiKey: WXNRMKHSILWHJQ-FSCRYUKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.06
• 重原子数：
  77.0
• 可旋转键数：
  49.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  218.76
• 氢给体数：
  3.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 、 Hexadecanoic acid (R)-2-[((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-(2-cyano-ethoxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 在 四氮唑 、 间氯过氧苯甲酸 作用下， 生成 2,6-O-bis(benzyloxymethyl)-3,4,5-O-tris(dibenzylphosphoryl)-D-myo-inositol 1-O-(1,2-O-dipalmitoyl)-sn-glyceryl 2-cyanoethyl phosphate
  参考文献：
  名称：

  Synthesis of Phosphotriester Analogues of the Phosphoinositides PtdIns(4,5)P₂ and PtdIns(3,4,5)P₃

  摘要：

  A synthetic route was developed for the preparation of novel O-(3-aminopropyl) tethered phosphotriester analogs (5) of phosphatidylinositol 4,5-bisphosphate (PtdIns(4,5,)P-2, or PIP2) and phosphatidylinositol 3,4,5-trisphosphate (PtdIns(3,4,5)P-3, or PIP3) using the coupling reagent 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite. The phosphotriester ligand design introduced a reactive aminopropyl group at the polar lipid head of the ring-phosphorylated phosphoinositides, allowing a reporter moiety to be positioned at the surface of the bilayer and in the vicinity of the phosphorylated inositol. Such reporter groups may interact with membrane-proximal regions of PIP2- and PIP3-binding proteins recruited to membrane sites by electrostatic interactions between the phosphates of the phospholipid and basic regions of the proteins. Following a convergent strategy, phosphitylation of an optically-pure 1,2-O-diacyl-sn-glycerol with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite was followed by coupling with protected inositol precursors to give adducts 8 in 80% to 95% yield. The 2-cyanoethyl phosphotriester was stable during the subsequent reaction steps and could be conveniently converted to the 3-aminopropyl group during the final hydrogenolysis of the benzyl protecting groups. Benzophenone-containing photoaffinity probes of the phosphotriester IIa and IIb were also synthesized. Alternatively, the versatile cyanoethyl group could be removed using diisopropylethylamine prior to hydrogenolysis, thereby furnishing the corresponding phosphodiesters, PIP3 and PIP2 (13a and 13b).

  DOI：

  10.1021/jo961226g
• 作为产物：
  描述：

  Hexadecanoic acid (R)-2-[[(1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-tris-(4-methoxy-benzyloxy)-cyclohexyloxy]-(2-cyano-ethoxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以85%的产率得到Hexadecanoic acid (R)-2-[((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-(2-cyano-ethoxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Synthesis of Phosphotriester Analogues of the Phosphoinositides PtdIns(4,5)P₂ and PtdIns(3,4,5)P₃

  摘要：

  A synthetic route was developed for the preparation of novel O-(3-aminopropyl) tethered phosphotriester analogs (5) of phosphatidylinositol 4,5-bisphosphate (PtdIns(4,5,)P-2, or PIP2) and phosphatidylinositol 3,4,5-trisphosphate (PtdIns(3,4,5)P-3, or PIP3) using the coupling reagent 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite. The phosphotriester ligand design introduced a reactive aminopropyl group at the polar lipid head of the ring-phosphorylated phosphoinositides, allowing a reporter moiety to be positioned at the surface of the bilayer and in the vicinity of the phosphorylated inositol. Such reporter groups may interact with membrane-proximal regions of PIP2- and PIP3-binding proteins recruited to membrane sites by electrostatic interactions between the phosphates of the phospholipid and basic regions of the proteins. Following a convergent strategy, phosphitylation of an optically-pure 1,2-O-diacyl-sn-glycerol with 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite was followed by coupling with protected inositol precursors to give adducts 8 in 80% to 95% yield. The 2-cyanoethyl phosphotriester was stable during the subsequent reaction steps and could be conveniently converted to the 3-aminopropyl group during the final hydrogenolysis of the benzyl protecting groups. Benzophenone-containing photoaffinity probes of the phosphotriester IIa and IIb were also synthesized. Alternatively, the versatile cyanoethyl group could be removed using diisopropylethylamine prior to hydrogenolysis, thereby furnishing the corresponding phosphodiesters, PIP3 and PIP2 (13a and 13b).

  DOI：

  10.1021/jo961226g