methyl (E)-5-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]pent-2-enoate | 881017-72-7

• 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: methyl (E)-5-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]pent-2-enoate
• CAS: 881017-72-7
• 化学式: C₁₇H₃₂O₄Si
• 分子量: 328.524
• InChiKey: QYOAAAMGDWAFJL-QQAGXBGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-5-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]pent-2-enoate 在 叔丁基过氧化氢 titanium(IV) isopropylate 、 D-(-)-酒石酸二乙酯 、 4 A molecular sieve 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 benzoic acid (1S,2R)-1-{2-[(2R,3S)-3-(tert-butyldimethylsilanyloxy)tetrahydropyran-2-yl]ethyl}-2,3-dihydroxypropyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Cyclic Ethers by Intramolecular Trapping of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations

  摘要：

  The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when additional stereocenters are present, providing iterative methodology to access ladder-like cyclic ethers.

  DOI：

  10.1021/jo0340556
• 作为产物：
  描述：

  3-[(2R,3S)-3-(tert-butyldimethylsilanyloxy)tetrahydropyran-2-yl]propan-1-ol 在 pyridine-SO3 complex 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 methyl (E)-5-[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]pent-2-enoate
  参考文献：
  名称：

  Stereoselective Synthesis of Cyclic Ethers by Intramolecular Trapping of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations

  摘要：

  The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when additional stereocenters are present, providing iterative methodology to access ladder-like cyclic ethers.

  DOI：

  10.1021/jo0340556

文献信息

• Cu(II)-mediated Stereoselective Michael Addition of a Methyl Group to an α,β-Unsaturated Ester as the C2-Side Chain in 3-(t-Butyldimethylsilyloxy)tetrahydropyrans
  作者：Tadashi Nakata、Keisuke Suzuki、Ulrike Jannsen、Hiroko Matsukura

  DOI：10.3987/com-05-s(k)45

  日期：——
• Stereoselective Synthesis of Cyclic Ethers by Intramolecular Trapping of Dicobalt Hexacarbonyl-Stabilized Propargylic Cations
  作者：Juan M. Betancort、Tomás Martín、José M. Palazón、Víctor S. Martín

  DOI：10.1021/jo0340556

  日期：2003.4.1

  The intramolecular attack of a hydroxy group on an exo-biscobalthexacarbonyl propargylic cation provides cyclic ethers with six- to nine-membered rings. The scope and limitations of the methodology are described. The reaction is stereoselective when additional stereocenters are present, providing iterative methodology to access ladder-like cyclic ethers.