(2S,3R,6S,8S)-8-tert-butyldimethylsilyloxy-3,6-epoxy-2-methylundecan-1-ol | 288577-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2S,3R,6S,8S)-8-tert-butyldimethylsilyloxy-3,6-epoxy-2-methylundecan-1-ol
• 英文别名: (2S)-2-[(2R,5S)-5-[(2S)-2-[tert-butyl(dimethyl)silyl]oxypentyl]oxolan-2-yl]propan-1-ol
• CAS: 288577-06-0
• 化学式: C₁₈H₃₈O₃Si
• 分子量: 330.583
• InChiKey: ROTOLRAJDWHFQL-LUKYLMHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (2S,3R,6S,8S)-8-tert-butyldimethylsilyloxy-3,6-epoxy-2-methylundecan-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 以96%的产率得到tert-butyl-[(2S)-1-[(2S,5R)-5-[(2R)-1-iodopropan-2-yl]oxolan-2-yl]pentan-2-yl]oxy-dimethylsilane
  参考文献：
  名称：

  A sultone approach to the C(1)–C(18) moiety of pamamycin-607

  摘要：

  A highly advanced enantiomerically pure C(1)-C(18) precursor of the larger fragment of the macro-diolide pamamycin-607 has been synthesized. The stereotriad C(7)-C(9) between the two heterocyclic rings of the target was generated using a diastereoselective hydroboration controlled by minimization of allylic 1,3-strain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00659-6
• 作为产物：
  描述：

  methyl (2R)-2-[(2R,5S)-5-[(2S)-2-hydroxypentyl]oxolan-2-yl]propanoate 在 4-二甲氨基吡啶 咪唑 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3R,6S,8S)-8-tert-butyldimethylsilyloxy-3,6-epoxy-2-methylundecan-1-ol
  参考文献：
  名称：

  A sultone approach to the C(1)–C(18) moiety of pamamycin-607

  摘要：

  A highly advanced enantiomerically pure C(1)-C(18) precursor of the larger fragment of the macro-diolide pamamycin-607 has been synthesized. The stereotriad C(7)-C(9) between the two heterocyclic rings of the target was generated using a diastereoselective hydroboration controlled by minimization of allylic 1,3-strain. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00659-6

文献信息

• Synthesis of the L-Acid (C1-C18) Fragment of Pamamycin-593 and De-<i>N</i>-methylpamamycin-579
  作者：Ayako Miura、Shin-ya Takigawa、Yukito Furuya、Yusuke Yokoo、Shigefumi Kuwahara、Hiromasa Kiyota

  DOI：10.1002/ejoc.200800600

  日期：2008.10

  The L-acid (C1–C18) fragment of pamamycin-593 and de-N-methylpamamycin-579, strong aerial mycelium-inducers of Streptomyces alboniger, was synthesized using a cis-selective iodoetherification and a nucleophilic addition of a cerium acetylide to an aldehyde as the key steps. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  pamamycin-593 和 de-N-methylpamamycin-579 的 L-酸（C1-C18）片段是 Streptomyces alboniger 的强气生菌丝诱导剂，使用顺式选择性碘醚化和乙炔铈亲核加成合成醛为关键步骤。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)