[(2R)-3-hexadecoxy-2-sulfanylpropyl] 2-(trimethylazaniumyl)ethyl phosphate | 177167-84-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [(2R)-3-hexadecoxy-2-sulfanylpropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 177167-84-9
• 化学式: C₂₄H₅₂NO₅PS
• 分子量: 497.72
• InChiKey: UQMIEFVSOOTXDI-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  花生四烯酸 、 [(2R)-3-hexadecoxy-2-sulfanylpropyl] 2-(trimethylazaniumyl)ethyl phosphate 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 3.0h， 以15.8 g的产率得到1-O-hexadecyl-2-thioarachidonyl-2-deoxy-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  A Stereoselective and Highly Practical Synthesis of Cytosolic Phospholipase A₂ Substrate, 2-S-Arachidonoyl-1-O-hexadecyl-sn-2-thioglycero-3-O-phosphocholine

  摘要：

  The substrate 1 of cytosolic phospholipase A(2) (cPLA(2)) is an ether-type thiophospholipid with arachidonic acid at the C-2 position and is required for the chromogenic assay for reliable and convenient high throughput screening. The original method of synthesis of 1 has significant problems, resulting in extremely low overall yield and purity. We developed a novel and highly practical method of preparing sufficient quantities of pure 1 for assay. Our synthetic sequence is started with commercially available 1,2-O-isopropylidene-sn-grycerol (5) and is based on the following key steps: trityl migration reaction of 10 with boron trifluoride etherate to form 13, phosphocholine-forming reaction of 13 to yield 15, and efficient conversion of 15 into 1 by deprotection of a trityl group and condensation with arachidonic acid. Our method offers a practical means of large-scale production of 1 with excellent high chemical purity, because of the introduction of arachidonic acid at the last step of the synthetic sequence.

  DOI：

  10.1021/jo970882t
• 作为产物：
  描述：

  S-[(2R)-1-hexadecoxy-3-trityloxypropan-2-yl] ethanethioate 在 吡啶 、 三氟化硼乙醚 、 硫化氢 、 sodium methylate 、 silver nitrate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 22.75h， 生成 [(2R)-3-hexadecoxy-2-sulfanylpropyl] 2-(trimethylazaniumyl)ethyl phosphate
  参考文献：
  名称：

  A Stereoselective and Highly Practical Synthesis of Cytosolic Phospholipase A₂ Substrate, 2-S-Arachidonoyl-1-O-hexadecyl-sn-2-thioglycero-3-O-phosphocholine

  摘要：

  The substrate 1 of cytosolic phospholipase A(2) (cPLA(2)) is an ether-type thiophospholipid with arachidonic acid at the C-2 position and is required for the chromogenic assay for reliable and convenient high throughput screening. The original method of synthesis of 1 has significant problems, resulting in extremely low overall yield and purity. We developed a novel and highly practical method of preparing sufficient quantities of pure 1 for assay. Our synthetic sequence is started with commercially available 1,2-O-isopropylidene-sn-grycerol (5) and is based on the following key steps: trityl migration reaction of 10 with boron trifluoride etherate to form 13, phosphocholine-forming reaction of 13 to yield 15, and efficient conversion of 15 into 1 by deprotection of a trityl group and condensation with arachidonic acid. Our method offers a practical means of large-scale production of 1 with excellent high chemical purity, because of the introduction of arachidonic acid at the last step of the synthetic sequence.

  DOI：

  10.1021/jo970882t

文献信息

• A Stereoselective and Highly Practical Synthesis of Cytosolic Phospholipase A₂ Substrate, 2-<i>S</i>-Arachidonoyl-1-<i>O</i>-hexadecyl-<i>sn</i>-2-thioglycero-3-<i>O</i>-phosphocholine
  作者：Masahiro Fuji、Fumihiko Watanabe,、Yasuhiko Fujii、Hiroshi Hashizume、Takayuki Okuno、Kazuhiro Shirahase、Isao Teshirogi、Mitsuaki Ohtani

  DOI：10.1021/jo970882t

  日期：1997.10.1

  The substrate 1 of cytosolic phospholipase A(2) (cPLA(2)) is an ether-type thiophospholipid with arachidonic acid at the C-2 position and is required for the chromogenic assay for reliable and convenient high throughput screening. The original method of synthesis of 1 has significant problems, resulting in extremely low overall yield and purity. We developed a novel and highly practical method of preparing sufficient quantities of pure 1 for assay. Our synthetic sequence is started with commercially available 1,2-O-isopropylidene-sn-grycerol (5) and is based on the following key steps: trityl migration reaction of 10 with boron trifluoride etherate to form 13, phosphocholine-forming reaction of 13 to yield 15, and efficient conversion of 15 into 1 by deprotection of a trityl group and condensation with arachidonic acid. Our method offers a practical means of large-scale production of 1 with excellent high chemical purity, because of the introduction of arachidonic acid at the last step of the synthetic sequence.