{(2R,4R,5S)-5-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-methanol | 1428737-87-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: {(2R,4R,5S)-5-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-methanol
• 英文别名: [(2R,4R,5S)-5-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-methyloxolan-2-yl]methanol
• CAS: 1428737-87-4
• 化学式: C₂₄H₃₄O₃Si
• 分子量: 398.618
• InChiKey: MUMPXYHWYZQDFU-VIZSFHNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {(2R,4R,5S)-5-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-methanol 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成 {(2R,4R,5S)-5-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}acetic acid
  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：

  2-{(2S,5R)-5-[(tert-butyldimethylsilyloxy)methyl]-3-methylenetetrahydrofuran-2-yl}-acetaldehyde 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 Crabtree's catalyst 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 {(2R,4R,5S)-5-[2-(tert-butyldiphenylsilyloxy)ethyl]-4-methyltetrahydrofuran-2-yl}-methanol
  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

• Synthesis of the C-1–C-17 Fragment of Amphidinolides C, C2, C3, and F
  作者：J. Stephen Clark、Guang Yang、Andrew P. Osnowski

  DOI：10.1021/ol4004838

  日期：2013.4.5

  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.