methyl (1S,2S,6S,9R,11S)-11-[(E)-3-methoxy-3-oxoprop-1-enyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecane-11-carboxylate | 864277-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: methyl (1S,2S,6S,9R,11S)-11-[(E)-3-methoxy-3-oxoprop-1-enyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecane-11-carboxylate
• CAS: 864277-26-9
• 化学式: C₁₆H₂₂O₈
• 分子量: 342.346
• InChiKey: POKWDXUMTRFXCR-YJXSFSSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (1S,2S,6S,9R,11S)-11-[(E)-3-methoxy-3-oxoprop-1-enyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecane-11-carboxylate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-diisopropyl tartrate 、 potassium tert-butylate 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 (3aS,5aR,7S,8aS,8bS)-7-[(R)-((R)-3-Benzyl-2-oxo-oxazolidin-4-yl)-hydroxy-methyl]-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of dysiherbaine analogue

  摘要：

  Synthesis of dysiherbaine analogue 4, which corresponds to 8,9-epi-neodysiherbaine A, is described. The synthesis features a concise route to the bicyclic ether skeleton through stereoselective C-glycosylation to set the C-6 stereocenter and 5-exo ring-closure to form the tetrahydrofuran ring. The results of preliminary biological studies of 4 are also provided. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.093
• 作为产物：
  描述：

  (3aS,5aR,7S,8aS,8bS)-methyl 7-{[(tert-butyldimethylsilyl)-oxy]methyl}-2,2-dimethylhexahydro-3aH-[1,3]dioxolo[4,5-d]furo[3,2-b]pyran-7-carboxylate 在 pyridine-SO3 complex 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl (1S,2S,6S,9R,11S)-11-[(E)-3-methoxy-3-oxoprop-1-enyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecane-11-carboxylate
  参考文献：
  名称：

  Synthesis of dysiherbaine analogue

  摘要：

  Synthesis of dysiherbaine analogue 4, which corresponds to 8,9-epi-neodysiherbaine A, is described. The synthesis features a concise route to the bicyclic ether skeleton through stereoselective C-glycosylation to set the C-6 stereocenter and 5-exo ring-closure to form the tetrahydrofuran ring. The results of preliminary biological studies of 4 are also provided. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.093

文献信息

• Synthesis of dysiherbaine analogue
  作者：Muneo Shoji、Kaoru Shiohara、Masato Oikawa、Ryuichi Sakai、Makoto Sasaki

  DOI：10.1016/j.tetlet.2005.06.093

  日期：2005.8

  Synthesis of dysiherbaine analogue 4, which corresponds to 8,9-epi-neodysiherbaine A, is described. The synthesis features a concise route to the bicyclic ether skeleton through stereoselective C-glycosylation to set the C-6 stereocenter and 5-exo ring-closure to form the tetrahydrofuran ring. The results of preliminary biological studies of 4 are also provided. (c) 2005 Elsevier Ltd. All rights reserved.