(R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate | 92445-93-7

• 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: (R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate
• 英文别名: [(2R)-1-hexadecoxy-3-trityloxypropan-2-yl] methanesulfonate
• CAS: 92445-93-7
• 化学式: C₃₉H₅₆O₅S
• 分子量: 636.937
• InChiKey: DTRXHEKVYKGWIM-KXQOOQHDSA-N

物化性质

• 沸点：
  715.1±60.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.84
• 重原子数：
  45.0
• 可旋转键数：
  25.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-3-(1-hexadecyloxy)-1-(trityloxy)propan-2-yl methanesulfonate 在 4-二甲氨基吡啶 、 sodium azide 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 6-(2-hydroxyethyl)-2-methyl-1,3,6,2-dioxazasilocan-2-ol 2-(o-tolyloxy)acetate
  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
• 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 (R)-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

• 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.