(2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-4-(2-iodoethyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxane | 1206481-48-2

• 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,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-4-(2-iodoethyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxane
• CAS: 1206481-48-2
• 化学式: C₃₁H₄₇IO₅Si
• 分子量: 654.701
• InChiKey: OISQMVWLMZQZPO-CNSBPHOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-Trimethylsilylethyl 3,4,6-trimethoxy-2-(phenylselanylmethyl)benzoate 、 (2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-4-(2-iodoethyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxane 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 生成 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
  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-((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)ethanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-4-(2-iodoethyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxane
  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