((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl pivalate | 1206481-31-3

• 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: ((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl pivalate
• CAS: 1206481-31-3
• 化学式: C₃₅H₅₄O₇Si
• 分子量: 614.895
• InChiKey: DPEVETFZRWPBIO-CANUFQTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.23
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl pivalate 在 二异丁基氢化铝 、 水 、 氯化铵 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)methanol
  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：

  ((2S,4R,5S,6S)-6-((R,E)-4-(tert-butyldimethylsilyloxy)-pent-1-enyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl pivalate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以98%的产率得到((2S,4R,5S,6S)-6-((R)-4-(tert-butyldimethylsilyloxy)-pentyl)-5-(4-methoxybenzyloxy)-2-phenyl-1,3-dioxan-4-yl)methyl pivalate
  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