[(2S,3R)-3-[(1S,2S,6S,9R,11R)-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecan-11-yl]oxiran-2-yl]methanol | 864277-22-5

• 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: [(2S,3R)-3-[(1S,2S,6S,9R,11R)-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecan-11-yl]oxiran-2-yl]methanol
• CAS: 864277-22-5
• 化学式: C₂₀H₃₆O₇Si
• 分子量: 416.587
• InChiKey: NBINSKSOHISQGB-UTWWDUHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,3R)-3-[(1S,2S,6S,9R,11R)-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecan-11-yl]oxiran-2-yl]methanol 在 potassium tert-butylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (R)-3-Benzyl-4-{(R)-[(3aS,5aR,7R,8aS,8bS)-7-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-yl]-hydroxy-methyl}-oxazolidin-2-one
  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：

  在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-diisopropyl tartrate 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 [(2S,3R)-3-[(1S,2S,6S,9R,11R)-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-4,4-dimethyl-3,5,8,12-tetraoxatricyclo[7.3.0.02,6]dodecan-11-yl]oxiran-2-yl]methanol
  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.