(4R,6S,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-ol | 528867-42-7

• 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,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-ol
• 英文别名: (4R,6S,8S,10S)-6,8,10-tris[[tert-butyl(dimethyl)silyl]oxy]pentacos-1-en-4-ol
• CAS: 528867-42-7
• 化学式: C₄₃H₉₂O₄Si₃
• 分子量: 757.458
• InChiKey: TXLDTRRUVYWGGU-BSUMSBOOSA-N

物化性质

• 沸点：
  668.2±55.0 °C(Predicted)
• 密度：
  0.881±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.75
• 重原子数：
  50
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,6S,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-ol 在 Grubbs catalyst first generation N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-5,6-dihydro-6-[(2S,4S,6S)-2,4,6-tris(tert-butyldimethylsilyloxy)heneicosyl]pyran-2-one
  参考文献：
  名称：

  Enantioselective allyltitanations: synthesis of the proposed structures for passifloricin A

  摘要：

  The stereoselective total synthesis of the proposed structures P1 and P2 for passifloricin A was achieved in 12 steps from n-hexadecanal by using enantioselective allyltitanations and a ring closing metathesis reaction as the key steps. Both PI and P2 are different from passifloricin A. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01024-4
• 作为产物：
  描述：

  十六醛 在 咪唑 、 2,6-二甲基吡啶 、 臭氧 、 (-)-diisopinocamphenylborane chloride 、 (+)-二异松蒎基氯硼烷 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 (4R,6S,8S,10S)-6,8,10-tris(tert-butyldimethylsilyloxy)pentacos-1-en-4-ol
  参考文献：
  名称：

  抗原选择性合成原虫内酯西番莲菌A及其七个异构体

  摘要：

  具有对原生动物活性的天然产物共轭的δ-内酯西番莲菌素A及其七个异构体以对映体纯的形式合成。已经表明以这种方式提出的天然化合物的结构是错误的。现在证明了正确的结构。合成的关键步骤是不对称的布朗型醛烯丙基化和闭环复分解。

  DOI：

  10.1021/jo049275d

文献信息

• On the Structure of Passifloricin A:  Asymmetric Synthesis of the δ-Lactones of (2<i>Z</i>,5<i>S</i>,7<i>R</i>,9<i>S</i>,11<i>S</i>)- and (2<i>Z</i>,5<i>R</i>,7<i>R</i>,9<i>S</i>,11<i>S</i>)-Tetrahydroxyhexacos-2-enoic Acid
  作者：Jorge García-Fortanet、Juan Murga、Miguel Carda、J. Alberto Marco

  DOI：10.1021/ol034182o

  日期：2003.5.1

  graphicStereoselective syntheses of the delta-lactone of (2Z,5S,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid, the structure reported for passifloricin A, and of its (5R)-epimer are described. The creation of all stereogenic centers relied upon Brown's asymmetric allylation methodology. The lactone ring was created via ring-closing metathesis. The NMR data of both synthetic products, however, were different from those of the natural product. The published structure of passifloricin A is thus erroneous and will require further synthetic work to be unambiguously assigned.
• Stereoselective Synthesis of the Antiprotozoal Lactone Passifloricin A and Seven Isomers Thereof
  作者：Juan Murga、Jorge García-Fortanet、Miguel Carda、J. Alberto Marco

  DOI：10.1021/jo049275d

  日期：2004.10.1

  The conjugated δ-lactone passifloricin A, a natural product with antiprotozoal activity, and seven isomers thereof have been synthesized in enantiopure form. It has been shown in this way that the proposed structure for the natural compound was erroneous. The correct structure is now evidenced. Key steps of the syntheses were asymmetric Brown-type aldehyde allylations and ring-closing metatheses.

  具有对原生动物活性的天然产物共轭的δ-内酯西番莲菌素A及其七个异构体以对映体纯的形式合成。已经表明以这种方式提出的天然化合物的结构是错误的。现在证明了正确的结构。合成的关键步骤是不对称的布朗型醛烯丙基化和闭环复分解。
• Enantioselective allyltitanations: synthesis of the proposed structures for passifloricin A
  作者：Samir BouzBouz、Janine Cossy

  DOI：10.1016/s0040-4039(03)01024-4

  日期：2003.6

  The stereoselective total synthesis of the proposed structures P1 and P2 for passifloricin A was achieved in 12 steps from n-hexadecanal by using enantioselective allyltitanations and a ring closing metathesis reaction as the key steps. Both PI and P2 are different from passifloricin A. (C) 2003 Elsevier Science Ltd. All rights reserved.