(2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal | 1309595-63-8

• 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: (2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal
• 英文别名: (2S,3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methyl-8-phenylmethoxyoctanal
• CAS: 1309595-63-8
• 化学式: C₂₈H₅₂O₄Si₂
• 分子量: 508.889
• InChiKey: RGBZVHVGCLERLH-ARMFNRFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1-溴基-1-丙烯 、 (2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal 在 碘 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (Z,5R,6S,8R)-6,8-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methyl-11-phenylmethoxyundec-2-en-4-ol 、
  参考文献：
  名称：

  Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C

  摘要：

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.

  DOI：

  10.1021/jo200466t
• 作为产物：
  描述：

  (R)-7-(benzyloxy)hept-1-en-4-ol 在 吡啶 、 咪唑 、 (4S,5S)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O^α)titanium 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 17.16h， 生成 (2R,3S,5R)-8-(benzyloxy)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-methyloctanal
  参考文献：
  名称：

  Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C

  摘要：

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.

  DOI：

  10.1021/jo200466t

文献信息

• Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C
  作者：Marie-Gabrielle Braun、Aurélie Vincent、Mehdi Boumediene、Joëlle Prunet

  DOI：10.1021/jo200466t

  日期：2011.6.17

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.