(2R,3S,4S,6S)-3,4-bis(phenylmethoxy)-6-[(1S)-1-phenylmethoxyethyl]-2-prop-2-enyloxane | 1076236-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,6S)-3,4-bis(phenylmethoxy)-6-[(1S)-1-phenylmethoxyethyl]-2-prop-2-enyloxane
• CAS: 1076236-61-7
• 化学式: C₃₁H₃₆O₄
• 分子量: 472.624
• InChiKey: HMIMYJXIPXJVMK-XKXKXQENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,6S)-3,4-bis(phenylmethoxy)-6-[(1S)-1-phenylmethoxyethyl]-2-prop-2-enyloxane 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以60%的产率得到2-[(2R,3S,4S,6S)-3,4-bis(phenylmethoxy)-6-[(1S)-1-phenylmethoxyethyl]oxan-2-yl]acetaldehyde
  参考文献：
  名称：

  Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment

  摘要：

  Model compounds (11 and 12) for the C1-C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1-C10 segment of the natural product possesses the 2R*,4R*,6R*,7S*,8R*,10S* relative configuration. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.035
• 作为产物：
  描述：

  (2S,3S,4S,6S)-2-methoxy-3,4-bis(phenylmethoxy)-6-[(1S)-1-phenylmethoxyethyl]oxane 、 烯丙基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以96%的产率得到(2R,3S,4S,6S)-3,4-bis(phenylmethoxy)-6-[(1S)-1-phenylmethoxyethyl]-2-prop-2-enyloxane
  参考文献：
  名称：

  Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment

  摘要：

  Model compounds (11 and 12) for the C1-C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1-C10 segment of the natural product possesses the 2R*,4R*,6R*,7S*,8R*,10S* relative configuration. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.035

文献信息

• Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment
  作者：Praveen Kommana、Seung Won Chung、William A. Donaldson

  DOI：10.1016/j.tetlet.2008.08.035

  日期：2008.10

  Model compounds (11 and 12) for the C1-C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1-C10 segment of the natural product possesses the 2R*,4R*,6R*,7S*,8R*,10S* relative configuration. (C) 2008 Elsevier Ltd. All rights reserved.