2-(trimethylsilyl)ethyl 2-((E)-3-((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)prop-1-enyl)-3,4,6-trimethoxybenzoate | 1206481-49-3

• 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: 2-(trimethylsilyl)ethyl 2-((E)-3-((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)prop-1-enyl)-3,4,6-trimethoxybenzoate
• 英文别名: 2-trimethylsilylethyl 2-[(E)-3-[(2S,4R,5S,6S)-6-[(4R)-4-[tert-butyl(dimethyl)silyl]oxypentyl]-5-[(4-methoxyphenyl)methoxy]-2-phenyl-1,3-dioxan-4-yl]prop-1-enyl]-3,4,6-trimethoxybenzoate
• CAS: 1206481-49-3
• 化学式: C₄₇H₇₀O₁₀Si₂
• 分子量: 851.238
• InChiKey: ZZXGILIFPAYCRB-VKZSFALMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.27
• 重原子数：
  59
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2-((E)-3-((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)prop-1-enyl)-3,4,6-trimethoxybenzoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到2-((E)-3-((2S,4R,5S,6S)-6-((R)-4-hydroxypentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)prop-1-enyl)-3,4,6-trimethoxybenzoic acid
  参考文献：
  名称：

  Synthesis of the proposed structure of queenslandon

  摘要：

  The proposed structure of the benzolactone queenslandon (6) was synthesized utilizing a triol containing building block prepared from D-ribose. While a ring-closing metathesis approach did not lead to the macrocycle, alkylation of a benzyl(phenyl)selane, elimination to generate the styrene double bond, followed by Mitsunobu macrolactonization proved to be successful. Spectral data suggest that the structure of queenslandon should be revised, probably to the C11 epimer. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.024
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2-(3-((2S,4R,5S,6S)-6-((R)-4-((tert-butyldimethylsilyl)oxy)pentyl)-5-((4-methoxybenzyl)oxy)-2-phenyl-1,3-dioxan-4-yl)-1-(phenylselanyl)propyl)-3,4,6-trimethoxybenzoate 在 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以85.5 mg的产率得到2-(trimethylsilyl)ethyl 2-((E)-3-((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)prop-1-enyl)-3,4,6-trimethoxybenzoate
  参考文献：
  名称：

  Synthesis of the proposed structure of queenslandon

  摘要：

  The proposed structure of the benzolactone queenslandon (6) was synthesized utilizing a triol containing building block prepared from D-ribose. While a ring-closing metathesis approach did not lead to the macrocycle, alkylation of a benzyl(phenyl)selane, elimination to generate the styrene double bond, followed by Mitsunobu macrolactonization proved to be successful. Spectral data suggest that the structure of queenslandon should be revised, probably to the C11 epimer. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.024

文献信息

• Synthesis of the proposed structure of queenslandon
  作者：Vaidotas Navickas、Martin E. Maier

  DOI：10.1016/j.tet.2009.11.024

  日期：2010.1

  The proposed structure of the benzolactone queenslandon (6) was synthesized utilizing a triol containing building block prepared from D-ribose. While a ring-closing metathesis approach did not lead to the macrocycle, alkylation of a benzyl(phenyl)selane, elimination to generate the styrene double bond, followed by Mitsunobu macrolactonization proved to be successful. Spectral data suggest that the structure of queenslandon should be revised, probably to the C11 epimer. (C) 2009 Elsevier Ltd. All rights reserved.