(2R,3S,4S,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-3-pyranol | 1082975-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2R,3S,4S,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-3-pyranol
• 英文别名: (2R,3S,4S,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydropyran-3-ol；(2R,3S,4S,5S)-4,5-bis(methoxymethoxy)-2-methyloxan-3-ol
• CAS: 1082975-52-7
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: ALEHLGUNEANKEE-XFWSIPNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-3-pyranol 、 在 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以0.05 mg的产率得到(2R,3S,4R,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-pyran-3-yl but-2-ynoate
  参考文献：
  名称：

  Stereoselective total synthesis of ophiocerin D from d-xylose

  摘要：

  A stereoselective total synthesis of ophiocerin D is reported by a combination of a 'chiron' approach and an asymmetric synthesis, from D-Xylose. Of the four stereogenic centers, the vic diols C3/C4 and C5/C6 were obtained by Sharpless asymmetric dihydroxylation and from D-Xylose, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.016
• 作为产物：
  描述：

  (2R,3S,4R,5S)-3-(benzyloxy)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-pyran 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以87%的产率得到(2R,3S,4S,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-3-pyranol
  参考文献：
  名称：

  Stereoselective total synthesis of ophiocerin D from d-xylose

  摘要：

  A stereoselective total synthesis of ophiocerin D is reported by a combination of a 'chiron' approach and an asymmetric synthesis, from D-Xylose. Of the four stereogenic centers, the vic diols C3/C4 and C5/C6 were obtained by Sharpless asymmetric dihydroxylation and from D-Xylose, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.016

文献信息

• A formal, stereoselective synthesis of the natural tetrahydropyran derivative ophiocerin D
  作者：Julián Paños、Juan Murga、Eva Falomir、Miguel Carda、J. Alberto Marco

  DOI：10.1016/j.tetasy.2010.01.013

  日期：2010.3

  A short, formal stereoselective synthesis of the naturally occurring tetrahydropyran derivative ophiocerin D is reported. The four stereocenters of the molecule were created with the aid of two Sharpless asymmetric dihydroxylations. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of ophiocerin D from d-xylose
  作者：Gangavaram V.M. Sharma、Krishna Damera

  DOI：10.1016/j.tetasy.2008.08.016

  日期：2008.9

  A stereoselective total synthesis of ophiocerin D is reported by a combination of a 'chiron' approach and an asymmetric synthesis, from D-Xylose. Of the four stereogenic centers, the vic diols C3/C4 and C5/C6 were obtained by Sharpless asymmetric dihydroxylation and from D-Xylose, respectively. (C) 2008 Elsevier Ltd. All rights reserved.