(1S,5S,7S)-7-benzyloxy-8,8-dimethyl-2,9-dioxabicyclo[3.3.1]nonan-3-one | 201422-11-9

• 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: (1S,5S,7S)-7-benzyloxy-8,8-dimethyl-2,9-dioxabicyclo[3.3.1]nonan-3-one
• 英文别名: (1S,5S,7S)-8,8-dimethyl-7-phenylmethoxy-2,9-dioxabicyclo[3.3.1]nonan-3-one
• CAS: 201422-11-9
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: PYYQVXSLTFYCSN-YDHLFZDLSA-N

物化性质

• 沸点：
  408.7±45.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1S,5S,7S)-7-benzyloxy-8,8-dimethyl-2,9-dioxabicyclo[3.3.1]nonan-3-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (4-benzyloxy-6-hydroxy-5,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 、 (4-benzyloxy-6-hydroxy-5,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o
• 作为产物：
  描述：

  (1S,3S,5S)-2,2-dimethyl-3-phenylmethoxy-8-oxabicyclo[3.2.1]oct-6-ene 在 sodium hydroxide 、 双氧水 、 silica gel 、 碳酸氢钠 、 diisopinocampheylborane 、 pyridinium chlorochromate 作用下， 生成 (1S,5S,7S)-7-benzyloxy-8,8-dimethyl-2,9-dioxabicyclo[3.3.1]nonan-3-one 、 (1S,5R,7R)-7-benzyloxy-6,6-dimethyl-2,9-dioxabicyclo[3.3.1]nonan-3-one
  参考文献：
  名称：

  Synthesis of the C1C9 segment of bryostatin

  摘要：

  The C1-C9 segment of bryostatin has been prepared in 11 steps in 21% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00564-8

文献信息

• Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins
  作者：A. Vakalopoulos、T. F. J. Lampe、H. M. R. Hoffmann

  DOI：10.1021/ol015551o

  日期：2001.3.1

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.
• Synthesis of the C1C9 segment of bryostatin
  作者：Jochen M. Weiss、H.M.R. Hoffmann

  DOI：10.1016/s0957-4166(97)00564-8

  日期：1997.12

  The C1-C9 segment of bryostatin has been prepared in 11 steps in 21% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.