(S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate | 92445-87-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate
• 英文别名: [(2S)-1-hexadecoxy-3-trityloxypropan-2-yl] methanesulfonate
• CAS: 92445-87-9
• 化学式: C₃₉H₅₆O₅S
• 分子量: 636.937
• InChiKey: DTRXHEKVYKGWIM-LHEWISCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  45
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate 在 三氟化硼乙醚 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 24.75h， 生成 2-((R)-3-Hexadecyloxy-2-tritylsulfanyl-propoxy)-[1,3,2]dioxaphospholane 2-oxide
  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：

  1-十六烷醇 在 吡啶 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (S)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate
  参考文献：
  名称：

  Structure and Synthesis of a Unique Isonitrile Lipid Isolated from the Marine Mollusk Actinocyclus papillatus

  摘要：

  The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.

  DOI：

  10.1021/ol200377w

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.
• Structure and Synthesis of a Unique Isonitrile Lipid Isolated from the Marine Mollusk <i>Actinocyclus papillatus</i>
  作者：Emiliano Manzo、Marianna Carbone、Ernesto Mollo、Carlo Irace、Antonio Di Pascale、Yan Li、Maria Letizia Ciavatta、Guido Cimino、Yue-Wei Guo、Margherita Gavagnin

  DOI：10.1021/ol200377w

  日期：2011.4.15

  The first chemical study of an Actinocyclidae nudibranch, Actinocyclus papillatus, resulted in the isolation of (-)-actisonitrile (1), a lipid based on a 1,3-propanediol ether skeleton. The structure was established by spectroscopic methods, whereas the absolute configuration of the chiral center was determined by comparing the optical properties of natural actisonitrile with those of (+)- and (-)-synthetic enantiomers, opportunely prepared. Both (-)- and (+)-actisonitrile were tested in preliminary in vitro cytotoxicity bioassays on tumor and nontumor mammalian cells.