ethyl (2Z)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-7-methyl-3-(trimethylsilylmethyl)octa-2,6-dienoate | 198693-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethyl (2Z)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-7-methyl-3-(trimethylsilylmethyl)octa-2,6-dienoate
• CAS: 198693-85-5
• 化学式: C₂₂H₄₄O₄Si₂
• 分子量: 428.76
• InChiKey: NWKHWCYQYFTRDU-XMHGGMMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-7-methyl-3-(trimethylsilylmethyl)octa-2,6-dienoate 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二异丙酯 作用下， 以87%的产率得到(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2-hydroxymethyl-3,3-dimethyl-oxiranyl)-3-trimethylsilanylmethyl-pent-2-enoic acid ethyl ester
  参考文献：
  名称：

  Siamyl Glyoxylate as an Efficient Enophile in the Lewis Acid Mediated Glyoxylate Ene-Reaction with Allylic Ethers. Application to the Synthesis of a Taxol A-Ring Subunit

  摘要：

  In contrast to other simple alkyl glyoxylates, siamyl glyoxylate (la) proved to be an effective enophile in the glyoxylate ene-reaction with the allylic ether 2a, which we earlier used for the synthesis of the A-ring subunit of taxol.

  DOI：

  10.1021/jo971082l
• 作为产物：
  描述：

  3-Methylbutan-2-yl 2-[tert-butyl(dimethyl)silyl]oxy-4-[(4-methoxyphenyl)methoxymethyl]-5-methylhex-4-enoate 在 bis(acetylacetonate)nickel(II) 、 四甲基乙二胺 、 potassium tert-butylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 ethyl (2Z)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)-7-methyl-3-(trimethylsilylmethyl)octa-2,6-dienoate
  参考文献：
  名称：

  Siamyl Glyoxylate as an Efficient Enophile in the Lewis Acid Mediated Glyoxylate Ene-Reaction with Allylic Ethers. Application to the Synthesis of a Taxol A-Ring Subunit

  摘要：

  In contrast to other simple alkyl glyoxylates, siamyl glyoxylate (la) proved to be an effective enophile in the glyoxylate ene-reaction with the allylic ether 2a, which we earlier used for the synthesis of the A-ring subunit of taxol.

  DOI：

  10.1021/jo971082l

文献信息

• Siamyl Glyoxylate as an Efficient Enophile in the Lewis Acid Mediated Glyoxylate Ene-Reaction with Allylic Ethers. Application to the Synthesis of a Taxol A-Ring Subunit
  作者：Johan Wennerberg、Magnus Polla、Torbjörn Frejd

  DOI：10.1021/jo971082l

  日期：1997.12.1

  In contrast to other simple alkyl glyoxylates, siamyl glyoxylate (la) proved to be an effective enophile in the glyoxylate ene-reaction with the allylic ether 2a, which we earlier used for the synthesis of the A-ring subunit of taxol.