[(2S,3S)-3-((1S,2R,3R,4R,5S)-2-(benzyloxy)-4-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1,3,5-trimethyl-7-octenyl)oxiran-2-yl]methanol | 1261156-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2S,3S)-3-((1S,2R,3R,4R,5S)-2-(benzyloxy)-4-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1,3,5-trimethyl-7-octenyl)oxiran-2-yl]methanol
• 英文别名: [(2S,3S)-3-[(2S,3R,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4,6-dimethyl-3-phenylmethoxynon-8-en-2-yl]oxiran-2-yl]methanol
• CAS: 1261156-52-8
• 化学式: C₂₇H₄₆O₄Si
• 分子量: 462.745
• InChiKey: YRRUFJNGWQPRPJ-ZDPSXAHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S,3S)-3-((1S,2R,3R,4R,5S)-2-(benzyloxy)-4-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1,3,5-trimethyl-7-octenyl)oxiran-2-yl]methanol 在 红铝 、 氯化铵 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到(3R,4R,5R,6R,7R,8S)-5-(benzyloxy)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4,6,8-trimethyl-10-undecene-1,3-diol
  参考文献：
  名称：

  Towards the total synthesis of etnangien: synthesis of C32–C42 fragment by using a desymmetrization strategy

  摘要：

  The construction of the C32-C42 fragment of etnangien is described using a desymmetrization strategy generating five stereogenic centers from a bicyclic lactone Another notable feature includes the use of the Sharpless asymmetric epoxidation to generate a stereogenic center at C40 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.003
• 作为产物：
  描述：

  (2E,4R,5R,6R,7R,8S)-5-(benzyloxy)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-4,6,8-trimethyl-2,10-undecadien-1-ol 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 过氧化氢异丙苯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到[(2S,3S)-3-((1S,2R,3R,4R,5S)-2-(benzyloxy)-4-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1,3,5-trimethyl-7-octenyl)oxiran-2-yl]methanol
  参考文献：
  名称：

  Towards the total synthesis of etnangien: synthesis of C32–C42 fragment by using a desymmetrization strategy

  摘要：

  The construction of the C32-C42 fragment of etnangien is described using a desymmetrization strategy generating five stereogenic centers from a bicyclic lactone Another notable feature includes the use of the Sharpless asymmetric epoxidation to generate a stereogenic center at C40 (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.003

文献信息

• Towards the total synthesis of etnangien: synthesis of C32–C42 fragment by using a desymmetrization strategy
  作者：Gowravaram Sabitha、Kurra Yadagiri、Martha Bhikshapathi、Gajangi Chandrashekhar、Jhillu Singh Yadav

  DOI：10.1016/j.tetasy.2010.10.003

  日期：2010.10

  The construction of the C32-C42 fragment of etnangien is described using a desymmetrization strategy generating five stereogenic centers from a bicyclic lactone Another notable feature includes the use of the Sharpless asymmetric epoxidation to generate a stereogenic center at C40 (C) 2010 Elsevier Ltd All rights reserved