16-hydroxy-geranylgeranyl tetrahydropyranyl ether | 118197-70-9

• 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: 16-hydroxy-geranylgeranyl tetrahydropyranyl ether
• 英文别名: (2E,6E,10E,14E)-2,6,10,14-tetramethyl-16-(oxan-2-yloxy)hexadeca-2,6,10,14-tetraen-1-ol
• CAS: 118197-70-9
• 化学式: C₂₅H₄₂O₃
• 分子量: 390.607
• InChiKey: NGMSDOGXKZTXQY-GQJXEJCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  16-hydroxy-geranylgeranyl tetrahydropyranyl ether 在 正丁基锂 、 titanium(III) chloride 作用下， 以 乙二醇二甲醚 为溶剂， 以23%的产率得到2,2'-(((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,18,22,26,30-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaene-1,32-diyl)bis(oxy))bis(tetrahydro-2H-pyran)
  参考文献：
  名称：

  三种无环全反式四萜二醇的合成，细菌脂质的假定前体

  摘要：

  三种无环全反式四萜二醇 A、B 和 C 已从香叶醇 (1) 合成，通过涉及六个不同的源自香叶醇的 C10 合成子的收敛方案，并通过三种不同类型的已知反应偶联：烯丙基取代碳负离子将氯化物 α 转化为砜、烯丙醇的复制以及 Pd(0) 催化的烯丙基碳酸酯与双稳定碳负离子的偶联。A、B 和 C 代表已知膜增强剂的假定系统发育前体，并且是香叶基香叶醇的三种可能的远端二羟基化二聚体：尾对尾、头对头和头对尾。

  DOI：

  10.1246/bcsj.61.141
• 作为产物：
  描述：

  tert-butyl-dimethyl-[(2E,6E,10E,14E)-2,6,10,14-tetramethyl-8-(4-methylphenyl)sulfonyl-16-(oxan-2-yloxy)hexadeca-2,6,10,14-tetraenoxy]silane 以81%的产率得到
  参考文献：
  名称：

  CHAPPE, BERTRAND;MUSIKAS, HELENE;MARIE, DOMINIQUE;OURISSON, GUY, BULL. CHEM. SOC. JAP., 61,(1988) N 1, 141-148

  摘要：

  DOI：

文献信息

• A Biomimetic Synthesis of Sacculatane Diterpenoids
  作者：Marina Grinco、Veaceslav Kulciţki、Nicon Ungur、Pavel F. Vlad、Margherita Gavagnin、Francesco Castelluccio、Guido Cimino

  DOI：10.1002/hlca.200890031

  日期：2008.2

  The biomimetic synthesis of sacculatane-type epimeric compounds 14a and 14b is reported. The key synthetic step is the low-temperature superacidic cyclization of (all-E)-ω-acetoxygeranylgeraniol 12 obtained in nine steps from geranyllinalool (13). The 19-acetoxysacculata-7,17-dien-11-ol (14a) could be an important and convenient starting compound for the synthesis of other sacculatane diterpenoids.

  已报道了acc草型的差向异构化合物14a和14b的仿生合成。关键的合成步骤是在九个步骤中从香叶薄荷醇（13）获得的（全-E）-ω-乙酰氧基香叶基香叶醇12的低温超酸性环化。19-乙酰氧基acculata-7,17-dien-11-ol（14a）可能是合成其他sacculatane二萜类化合物的重要且方便的起始化合物。
• Synthesis from geraniol of (2E,6E,10E,14E)-16-hydroxygeranylgeraniol and some of its derivatives
  作者：M. Grin’ko、V. Kulcitki、N. Ungur、A. Barba、K. Delyanu、P. F. Vlad

  DOI：10.1007/s10600-007-0104-3

  日期：2007.5

  Several α,ω-bifunctional derivatives of E,E,E-geranylgeraniol were prepared via convergent synthesis starting with geraniol (8), which was converted in three steps into the tetrahydropyranyl ether of 8-chlorogeraniol (9) and 8-hydroxygeranylphenylsulfone (10). Combination of synthons 9 and 10 with subsequent reductive removal of the phenylsulfonyl group produced the tetrahydropyranyl ether of ω-hydroxygeranylgeraniol (5), hydrolysis of which gave exclusively trans-ω-hydroxygeranylgeraniol (1). Derivatives 5–7 of geranylgeraniol were synthesized using standard methods.

  以香叶醇（8）为起始原料，通过收敛合成法制备了E,E,E-香叶基香叶醇的几种α,ω-双官能衍生物，香叶醇（8）通过三个步骤转化为8-氯香叶醇（9）和8-羟基香叶基苯基砜（10）的四氢吡喃基醚。将合成单元9和10组合，随后还原去除苯基砜基，得到ω-羟基香叶基香叶醇（5）的四氢吡喃基醚，水解后得到纯反式-ω-羟基香叶基香叶醇（1）。香叶基香叶醇的衍生物5-7采用标准方法合成。
• Synthesis and Biological Activity of Photoactivatable <i>N</i>-Ras Peptides and Proteins
  作者：Martin Völkert、Koji Uwai、Andreas Tebbe、Boriana Popkirova、Melanie Wagner、Jürgen Kuhlmann、Herbert Waldmann

  DOI：10.1021/ja036178d

  日期：2003.10.1

  A modular strategy for the assembly of farnesylated N-Ras heptapeptides carrying a photo-activatable benzophenone (BP) group within the lipid residue is described. This strategy is based on the fragment condensation of a N-terminal hexapeptide synthesized on the solid support with a cysteine methyl ester which is modified with different farnesyl analogues, incorporating the photophor. At the N-terminus of the peptides different functional groups can be attached, e.g., biotin for product enrichment and detection after photoactivation or a maleimido (MIC) linker, allowing for the coupling to proteins carrying a C-terminal free cysteine. Using this strategy, 24 peptides were synthesized, incorporating famesyl analogues with four different chain lengths. Two of these photoactivatable conjugates were ligated to oncogenic human N-RasG12VDelta181. A cellular transformation assay revealed that the semisynthetic proteins retain their biological activity despite the photolabel. The first photolabeling experiments with a geranyl-BP-labeled N-Ras construct and the farnesyl-sensitive guanine nucleotide exchange factor hSos1 indicate that this photoaffinity labeling system can be particularly useful for studying protein-protein interactions, e.g., the participation of the farnesyl group in Ras signaling, which is still discussed with controversy.
• SATO, AKIO;NAKAJIMA, KENJI;TAKAHARA, YOSHIMASA;KIJIMA, SHIZUMASA;KUWANA, +
  作者：SATO, AKIO、NAKAJIMA, KENJI、TAKAHARA, YOSHIMASA、KIJIMA, SHIZUMASA、KUWANA, +

  DOI：——

  日期：——