(3R,4E,6E)-1-[tert-butyl(dimethyl)silyl]oxy-7-iodo-6-methylhepta-4,6-dien-3-ol | 201936-23-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,4E,6E)-1-[tert-butyl(dimethyl)silyl]oxy-7-iodo-6-methylhepta-4,6-dien-3-ol
• CAS: 201936-23-4
• 化学式: C₁₄H₂₇IO₂Si
• 分子量: 382.357
• InChiKey: SVMNQHHSXFFPGX-CULXKKOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4E,6E)-1-[tert-butyl(dimethyl)silyl]oxy-7-iodo-6-methylhepta-4,6-dien-3-ol 在 四丁基氟化铵 、 potassium hydride 作用下， 生成 (4E,6E)-(R)-7-Iodo-3-methoxy-6-methyl-hepta-4,6-dien-1-ol
  参考文献：
  名称：

  Convergent synthesis of the C31C46 domain of the phorboxazole natural products

  摘要：

  A convergent synthesis of the C31-C46 domain of the phorboxazole natural products has been developed. This involved the preparation of a C39-C46 dienyl iodide and a C31-C37 aldehyde, followed by their CrCl2-mediated coupling and final installation of the C46 (E)-vinyl bromide via an alkyne hydrostannation-bromination sequence. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10519-6
• 作为产物：
  描述：

  (4E,6E)-1-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-6-methyl-hepta-4,6-dien-3-one 在 (S)-(+)-alpha,alpha-二苯基脯氨醇 、 硼烷 作用下， 生成 (3R,4E,6E)-1-[tert-butyl(dimethyl)silyl]oxy-7-iodo-6-methylhepta-4,6-dien-3-ol
  参考文献：
  名称：

  Convergent synthesis of the C31C46 domain of the phorboxazole natural products

  摘要：

  A convergent synthesis of the C31-C46 domain of the phorboxazole natural products has been developed. This involved the preparation of a C39-C46 dienyl iodide and a C31-C37 aldehyde, followed by their CrCl2-mediated coupling and final installation of the C46 (E)-vinyl bromide via an alkyne hydrostannation-bromination sequence. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10519-6

文献信息

• Total Synthesis of Phorboxazole A via <i>de Novo</i> Oxazole Formation: Strategy and Component Assembly
  作者：Bo Wang、T. Matthew Hansen、Ting Wang、Dimao Wu、Lynn Weyer、Lu Ying、Mary M. Engler、Melissa Sanville、Christopher Leitheiser、Mathias Christmann、Yingtao Lu、Jiehao Chen、Nicholas Zunker、Russell D. Cink、Feryan Ahmed、Chi-Sing Lee、Craig J. Forsyth

  DOI：10.1021/ja108906e

  日期：2011.2.9

  The phorboxazole natural products are among the most potent inhibitors of cancer cell division, but they are essentially unavailable from natural sources at present. Laboratory syntheses based upon tri-component fragment coupling strategies have been developed that provide phorboxazole A and analogues in a reliable manner and with unprecedented efficiency. This has been orchestrated to occur via the

  佛盒唑天然产物是癌细胞分裂最有效的抑制剂之一，但目前基本上无法从天然来源获得。已经开发了基于三组分片段偶联策略的实验室合成，以可靠的方式和前所未有的效率提供佛盒唑 A 和类似物。这是通过从两个丝氨酸衍生的酰胺依次或同时形成天然产物的两个恶唑部分来进行的，包括氧化-环化脱水。已经开发了代表碳 3-17、18-30 和 31-46 的三种预组装组件的优化制备。本文详细介绍了这三个基本构建块的设计和综合。