(1S,2R)-1-[(2R,4R,5S)-4-methyl-5-(2-phenylmethoxyethyl)oxolan-2-yl]-2-phenylmethoxybut-3-en-1-ol | 1198097-24-3

• 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,2R)-1-[(2R,4R,5S)-4-methyl-5-(2-phenylmethoxyethyl)oxolan-2-yl]-2-phenylmethoxybut-3-en-1-ol
• CAS: 1198097-24-3
• 化学式: C₂₅H₃₂O₄
• 分子量: 396.527
• InChiKey: NALFARKATQLIDM-HYOIWIKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-[(2R,4R,5S)-4-methyl-5-(2-phenylmethoxyethyl)oxolan-2-yl]-2-phenylmethoxybut-3-en-1-ol 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以94%的产率得到(2S,3R,5R)-5-[(1S,2R)-1-[(4-methoxyphenyl)methoxy]-2-phenylmethoxybut-3-enyl]-3-methyl-2-(2-phenylmethoxyethyl)oxolane
  参考文献：
  名称：

  Stereoselective synthesis of the densely functionalized C1–C9 fragment of amphidinolides C and F

  摘要：

  The synthesis of the C1-C9 subunit of amphidinolides C and F is described. Key steps include tandem Sharpless asymmetric dihydroxylation-S(N)2 cyclization reaction, Lewis acid-mediated epoxide opening, Wittig reaction, and Wacker oxidation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.001
• 作为产物：
  描述：

  (2S,3R,5R)-5-[(2S,3S)-3-ethenyloxiran-2-yl]-3-methyl-2-(2-phenylmethoxyethyl)oxolane 、 苯甲醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以75%的产率得到(1S,2R)-1-[(2R,4R,5S)-4-methyl-5-(2-phenylmethoxyethyl)oxolan-2-yl]-2-phenylmethoxybut-3-en-1-ol
  参考文献：
  名称：

  Stereoselective synthesis of the densely functionalized C1–C9 fragment of amphidinolides C and F

  摘要：

  The synthesis of the C1-C9 subunit of amphidinolides C and F is described. Key steps include tandem Sharpless asymmetric dihydroxylation-S(N)2 cyclization reaction, Lewis acid-mediated epoxide opening, Wittig reaction, and Wacker oxidation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.001

文献信息

• Stereoselective synthesis of the densely functionalized C1–C9 fragment of amphidinolides C and F
  作者：Debendra K. Mohapatra、Pavankumar Dasari、Hasibur Rahaman、Rita Pal

  DOI：10.1016/j.tetlet.2009.09.001

  日期：2009.11

  The synthesis of the C1-C9 subunit of amphidinolides C and F is described. Key steps include tandem Sharpless asymmetric dihydroxylation-S(N)2 cyclization reaction, Lewis acid-mediated epoxide opening, Wittig reaction, and Wacker oxidation. (C) 2009 Elsevier Ltd. All rights reserved.