(S)-(-)-dolichol-20 | 89363-39-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-(-)-dolichol-20
• 英文别名: alpha-Dihydroeicosaprenol；(3S,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70E,74E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-ol
• CAS: 89363-39-3
• 化学式: C₁₀₀H₁₆₄O
• 分子量: 1382.4
• InChiKey: KEVPZUBEAUSPNJ-YETSSXBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  36.6
• 重原子数：
  101
• 可旋转键数：
  59
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以82%的产率得到(S)-(-)-dolichol-20
  参考文献：
  名称：

  Total Syntheses of C60- and C100-Dolichols

  摘要：

  C60- and C100-dolichols were synthesized. A Z-selective Wittig reaction was achieved with high selectivity in a microflow system to realize the scalable supply of the Z-isoprene unit. An isoprene chain was efficiently elongated by an S(N)2-type coupling between allyl sulfone and allyl chloride using t-BuOK. These key reactions enabled the efficient syntheses of dolichols. This study will pave the way for the functional studies of dolichols.

  DOI：

  10.1021/acs.joc.0c01327

文献信息

• Synthesis of mammalian dolichols from plant polyprenols
  作者：Shigeaki Suzuki、Fumio Mori、Tetsuo Takigawa、Koichi Ibata、Yoichi Ninagawa、Takashi Nishida、Masao Mizuno、Yasuyuki Tanaka

  DOI：10.1016/s0040-4039(00)94052-8

  日期：1983.1
• Total Syntheses of C60- and C100-Dolichols
  作者：Kohtaro Hirao、Risako Ono、Yoshiyuki Manabe、Seiji Masui、Haruyuki Atomi、Koichi Fukase

  DOI：10.1021/acs.joc.0c01327

  日期：2020.9.4

  C60- and C100-dolichols were synthesized. A Z-selective Wittig reaction was achieved with high selectivity in a microflow system to realize the scalable supply of the Z-isoprene unit. An isoprene chain was efficiently elongated by an S(N)2-type coupling between allyl sulfone and allyl chloride using t-BuOK. These key reactions enabled the efficient syntheses of dolichols. This study will pave the way for the functional studies of dolichols.