(2S)-2-[4-((tert-butyldiphenylsilyl)oxy)butyl] oxirane | 958635-23-9

• 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: (2S)-2-[4-((tert-butyldiphenylsilyl)oxy)butyl] oxirane
• 英文别名: tert-butyl-[4-[(2S)-oxiran-2-yl]butoxy]-diphenylsilane
• CAS: 958635-23-9
• 化学式: C₂₂H₃₀O₂Si
• 分子量: 354.565
• InChiKey: BVRKEPRZYCVVDQ-IBGZPJMESA-N

物化性质

• 沸点：
  410.4±27.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-[4-((tert-butyldiphenylsilyl)oxy)butyl] oxirane 在 sodium tetrahydroborate 、 正丁基锂 、 dilithium tetrachlorocuprate 、 四丁基氟化铵 、 sodium hydride 、 戴斯-马丁氧化剂 、 溶剂黄146 、 L-脯氨酸 、 scandium tris(trifluoromethanesulfonate) 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 、 甲苯 、 mineral oil 为溶剂， 反应 22.92h， 生成 (3S,6S)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol
  参考文献：
  名称：

  总合成和修订Seimatopolide B †的绝对构型

  摘要：

  从容易获得开始描述了天然Seimatopolide B及其对映异构体的不对称全合成 5-己烯-1-醇 和 3-丁-1-醇。涉及的关键步骤是Jacobson水解动力学拆分，脯氨酸催化的α-羟基化，山口酯化和闭环易位。这种不对称的总合成需要将最初分配的（3 R，6 S，9 S）-构型修改为（3 S，6 R，9 R）。

  DOI：

  10.1039/c3ob27518c
• 作为产物：
  描述：

  tert-butyl(hex-5-enyloxy)diphenylsilane 在 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 16.0h， 生成 (2S)-2-[4-((tert-butyldiphenylsilyl)oxy)butyl] oxirane
  参考文献：
  名称：

  Non-natural Acetogenin Analogues as PotentTrypanosoma bruceiInhibitors

  摘要：

  AbstractNeglected tropical diseases remain a serious global health concern. Here, a series of novel bis‐tetrahydropyran 1,4‐triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are detailed. The analogues synthesized display low micromolar trypanocidal activities towards both bloodstream and insect forms of Trypanosoma brucei, the causative agent of African sleeping sickness, also known as Human African Trypanosomiasis (HAT). A divergent synthetic strategy was adopted for the synthesis of the key tetrahydropyran intermediates to enable rapid access to diastereochemical variation either side of the 1,4‐triazole core. The resulting diastereomeric analogues displayed varying degrees of trypanocidal activity and selectivity in structure–activity relationship studies. Together, the biological potency and calculated lipophilicity values indicate that while there is room for improvement, these derivatives may represent a promising novel class of anti‐HAT agents.

  DOI：

  10.1002/cmdc.201402272

文献信息

• “Cassette” In Situ Enzymatic Screening Identifies Complementary Chiral Scaffolds for Hydrolytic Kinetic Resolution Across a Range of Epoxides
  作者：Sangeeta Dey、Douglas R. Powell、Chunhua Hu、David B. Berkowitz

  DOI：10.1002/anie.200701280

  日期：2007.9.17

  ‘Cassette’-ISES (In Situ Enzymatic Screening) Identifies Complementary Chiral Scaffolds for Hydrolytic Kinetic Resolution Across a Range of Epoxides A new ‘Cassette’-In Situ Enzymatic Screen (ISES) for combinatorial catalysis is introduced. This allows the experimentalist to obtain an information-rich readout, in real time, providing an estimate of the sense and magnitude of enantioselectivity across more than one substrate. In its first iteration, the screen identified CoIII-salen catalysts with β-pinene- and α-naphthylalanine-derived chiral scaffolds with broad, yet complementary, substrate specificities.
• Non-natural Acetogenin Analogues as Potent<i>Trypanosoma brucei</i>Inhibitors
  作者：Gordon J. Florence、Andrew L. Fraser、Eoin R. Gould、Elizabeth F. B. King、Stefanie K. Menzies、Joanne C. Morris、Lindsay B. Tulloch、Terry K. Smith

  DOI：10.1002/cmdc.201402272

  日期：2014.11

  AbstractNeglected tropical diseases remain a serious global health concern. Here, a series of novel bis‐tetrahydropyran 1,4‐triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are detailed. The analogues synthesized display low micromolar trypanocidal activities towards both bloodstream and insect forms of Trypanosoma brucei, the causative agent of African sleeping sickness, also known as Human African Trypanosomiasis (HAT). A divergent synthetic strategy was adopted for the synthesis of the key tetrahydropyran intermediates to enable rapid access to diastereochemical variation either side of the 1,4‐triazole core. The resulting diastereomeric analogues displayed varying degrees of trypanocidal activity and selectivity in structure–activity relationship studies. Together, the biological potency and calculated lipophilicity values indicate that while there is room for improvement, these derivatives may represent a promising novel class of anti‐HAT agents.
• Total synthesis and revision of the absolute configuration of seimatopolide B
  作者：Chada Raji Reddy、Uredi Dilipkumar、Motatipally Damoder Reddy、Nagavaram Narsimha Rao

  DOI：10.1039/c3ob27518c

  日期：——

  steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxylation, Yamaguchi esterification and ring-closing metathesis. This asymmetric total synthesis necessitates the revision of the originally assigned (3R, 6S, 9S)-configuration to (3S, 6R, 9R).

  从容易获得开始描述了天然Seimatopolide B及其对映异构体的不对称全合成 5-己烯-1-醇 和 3-丁-1-醇。涉及的关键步骤是Jacobson水解动力学拆分，脯氨酸催化的α-羟基化，山口酯化和闭环易位。这种不对称的总合成需要将最初分配的（3 R，6 S，9 S）-构型修改为（3 S，6 R，9 R）。