2-{(2S,3R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-3-methyltetrahydrofuran-2-yl}-ethanol | 1198097-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-{(2S,3R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-3-methyltetrahydrofuran-2-yl}-ethanol
• CAS: 1198097-15-2
• 化学式: C₁₄H₃₀O₃Si
• 分子量: 274.476
• InChiKey: DTSKCEYVRCJBAL-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-{(2S,3R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-3-methyltetrahydrofuran-2-yl}-ethanol 在 4-二甲氨基吡啶 、 氢气 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 40.5h， 生成
  参考文献：
  名称：

  Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F

  摘要：

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.

  DOI：

  10.1021/ol4004838
• 作为产物：
  描述：

  3-{(2S,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-3-methylenetetrahydrofuran-2-yl}-propane-1,2-diol 在 sodium tetrahydroborate 、 sodium periodate 、 Crabtree's catalyst 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 2-{(2S,3R,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-3-methyltetrahydrofuran-2-yl}-ethanol
  参考文献：
  名称：

  Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F

  摘要：

  The C-1-C-17 fragment of amphidinolides C, C2, C3, and F has been constructed from a trans-2,5-disubstituted dihydrofuranone prepared by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The dihydrofuranone was converted into an aldehyde corresponding to the C-1-C-8 framework, and this was coupled to the C-9-C-17 unit by nucleophilic addition of a vinylic anion.

  DOI：

  10.1021/ol4004838

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.