(4R,6S,7R,8R,12R)-4,6-bis((tert-butyldimethylsilyl)oxy)-8-(methoxymethoxy)-7,10-dimethyl-12-(triethylsilyloxy)pentadec-9-en-1-ol | 1309595-67-2

• 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: (4R,6S,7R,8R,12R)-4,6-bis((tert-butyldimethylsilyl)oxy)-8-(methoxymethoxy)-7,10-dimethyl-12-(triethylsilyloxy)pentadec-9-en-1-ol
• 英文别名: (E,4R,6S,7R,8R,12R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-8-(methoxymethoxy)-7,10-dimethyl-12-triethylsilyloxypentadec-9-en-1-ol
• CAS: 1309595-67-2
• 化学式: C₃₇H₈₀O₆Si₃
• 分子量: 705.295
• InChiKey: AXQALTJGNOTAPP-KXWUHSOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.08
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,6S,7R,8R,12R)-4,6-bis((tert-butyldimethylsilyl)oxy)-8-(methoxymethoxy)-7,10-dimethyl-12-(triethylsilyloxy)pentadec-9-en-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以72%的产率得到(5R,9R,10R,11S,13R)-11-((tert-butyldimethylsilyl)oxy)-3,3-diethyl-13-(3-iodopropyl)-9-(methoxymethoxy)-7,10,15,15,16,16-hexamethyl-5-propyl-4,14-dioxa-3,15-disilaheptadec-7-ene
  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)-1,2-环氧基戊烷 在 copper(l) iodide 、 Hoveyda-Grubbs catalyst second generation 、 氢气 、 L-Selectride 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， -78.0~50.0 ℃ 、101.33 kPa 条件下， 反应 85.5h， 生成 (4R,6S,7R,8R,12R)-4,6-bis((tert-butyldimethylsilyl)oxy)-8-(methoxymethoxy)-7,10-dimethyl-12-(triethylsilyloxy)pentadec-9-en-1-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

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.