(4S,5R,6S,Z)-5,7-bis((tert-butyldimethylsilyl)oxy)-2,4,6-trimethylhept-2-en-1-ol | 443761-83-9

• 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: (4S,5R,6S,Z)-5,7-bis((tert-butyldimethylsilyl)oxy)-2,4,6-trimethylhept-2-en-1-ol
• 英文别名: (Z,4S,5R,6S)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-2,4,6-trimethylhept-2-en-1-ol
• CAS: 443761-83-9
• 化学式: C₂₂H₄₈O₃Si₂
• 分子量: 416.792
• InChiKey: OSDDHSJTULTMHH-LGIUGZTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (4S,5R,6S,Z)-5,7-bis((tert-butyldimethylsilyl)oxy)-2,4,6-trimethylhept-2-en-1-ol 在 palladium on activated charcoal 吗啉 、 吡啶 、 2,6-二甲基吡啶 、 chromium dichloride 、 盐酸 、 aluminum oxide 、 草酰氯 、 lithium bis(dimethylphenylsilyl)amide 、 Jones oxidant 、 pH 7 buffer 、 氢氟酸 、 potassium tert-butylate 、 氢气 、 碘 、 二异丁基氢化铝 、 碳酸氢钠 、 二甲基亚砜 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 mercury dichloride 、 lithium bromide 、 nickel dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 145.92h， 生成 盘皮海绵内酯
  参考文献：
  名称：

  Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization

  摘要：

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.

  DOI：

  10.1021/ja961374o
• 作为产物：
  描述：

  (2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol 在 吡啶 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 二甲基硫 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 (4S,5R,6S,Z)-5,7-bis((tert-butyldimethylsilyl)oxy)-2,4,6-trimethylhept-2-en-1-ol
  参考文献：
  名称：

  Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization

  摘要：

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.

  DOI：

  10.1021/ja961374o

文献信息

• Synthesis of (+)-Discodermolide by Catalytic Stereoselective Borylation Reactions
  作者：Zhiyong Yu、Robert J. Ely、James P. Morken

  DOI：10.1002/anie.201405455

  日期：2014.9.1

  1990 and, to this day, remains a compelling synthesis target. Not only does the compound possess fascinating biological activity, but it also presents an opportunity to test current methods for chemical synthesis and provides an inspiration for new reaction development. A new synthesis of discodermolide employs a previously undisclosed stereoselective catalytic diene hydroboration and also establishes

  海洋天然产物 (+)-discodermolide 于 1990 年首次分离出来，至今仍是一个引人注目的合成目标。该化合物不仅具有令人着迷的生物活性，而且还为测试现有化学合成方法提供了机会，并为新反应的开发提供了灵感。 discodermolide 的新合成采用了先前未公开的立体选择性催化二烯硼氢化反应，并且还建立了手性烯醇化物烷基化的策略。此外，discodermolide 的这种合成提供了复杂分子合成中二烯不对称 1,4-二硼化和硼基化二烯-醛偶联的第一个例子。
• Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization
  作者：Deborah T. Hung、Jennie B. Nerenberg、Stuart L. Schreiber

  DOI：10.1021/ja961374o

  日期：1996.11.13

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.