(2R,3S,4R,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-pyran-3-yl but-2-ynoate | 1082975-74-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4R,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-pyran-3-yl but-2-ynoate
• 英文别名: [(2R,3S,4R,5S)-4,5-bis(methoxymethoxy)-2-methyloxan-3-yl] but-2-ynoate
• CAS: 1082975-74-3
• 化学式: C₁₄H₂₂O₇
• 分子量: 302.324
• InChiKey: VTXQIKBNOXPEST-UVLXDEKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-pyran-3-yl but-2-ynoate 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以75%的产率得到(2R,3S,4R,5S)-4,5-bis(methoxymethoxy)-2-methyltetrahydro-2H-pyran-3-yl (Z)-but-2-enoate
  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,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

文献信息

• 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.