(S)-3-t-butyldimethylsilyloxy-γ-butyrolactone | 122654-37-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (S)-3-t-butyldimethylsilyloxy-γ-butyrolactone
• 英文别名: 3-(S)-O-{[(1,1-dimethyl)ethyl dimethylsilyl]oxy}-γ-butyrolactone；(4S)-4-[tert-butyl(dimethyl)silyl]oxyoxolan-2-one
• CAS: 122654-37-9
• 化学式: C₁₀H₂₀O₃Si
• 分子量: 216.352
• InChiKey: UYTSKHVZHALIDM-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-t-butyldimethylsilyloxy-γ-butyrolactone 在 肼 作用下， 以 乙醇 为溶剂， 生成 (S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-butyric acid hydrazide
  参考文献：
  名称：

  Yamada, Haruo; Sugiyama, Hajime; Kajiwara, Masahiro, Heterocycles, 1987, vol. 26, # 11, p. 2841 - 2844

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-(-)-β-羟基-γ-丁内酯 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-3-t-butyldimethylsilyloxy-γ-butyrolactone
  参考文献：
  名称：

  Yamada, Haruo; Sugiyama, Hajime; Kajiwara, Masahiro, Heterocycles, 1987, vol. 26, # 11, p. 2841 - 2844

  摘要：

  DOI：

文献信息

• Asymmetric Synthesis of 14-A_4t-Neuroprostane:  Hunting for a Suitable Biomarker for Neurodegenerative Diseases
  作者：Giuseppe Zanoni、Enrico M. Brunoldi、Alessio Porta、Giovanni Vidari

  DOI：10.1021/jo701719f

  日期：2007.12.1

  describe the first total synthesis of 14-A4t-NeuroP in an enantioselective and stereoselective fashion, by means of a new and rapid approach for the installation of the ω chain based on a chemoselective Julia−Kocienski olefination. Furthermore, the construction of the 4,5-cis-disubstituted cyclopentenone moiety characteristic of class A neuroprostanes is achieved in a stereospecific fashion, and suitable

  长期以来，氧化应激与衰老和与年龄有关的病理（例如神经退行性疾病）有关。体内氧化应激的直接作用之一是通过活性氧对膜磷脂的作用形成称为异前列腺素的前列腺素样化合物。由二十二碳六烯酸（C22：6ω3，DHA）形成的异前列腺素的一个特殊亚类，称为神经前列腺素，被认为对神经元氧化应激具有特异性。由于异前列腺素被认为是氧化应激的黄金标准，并且由于神经前列腺素在神经元中对这种状况的特异性及其与阿尔茨海默氏病和帕金森氏病的关系，因此可以预见它们将是这些病理学的合适生物标志物。在这里，我们描述了14-A 4t的第一个全合成-NeuroP以对映选择性和立体选择性的方式，通过一种新的快速方法来安装基于化学选择性Julia-Kocienski烯烃的ω链。此外，以立体特异性方式实现了A类神经前列腺素特征性的4，5-顺式-二取代的环戊烯酮部分的构建，并且已经调整了合适的反应条件以避免不稳定的立体异构中心的差向异构化。
• A New Reaction Manifold for the Barton Radical Intermediates:  Synthesis of <i>N</i>-Heterocyclic Furanosides and Pyranosides via the Formation of the C₁−C₂ Bond
  作者：Jong Uk Rhee、Brian I. Bliss、T. V. RajanBabu

  DOI：10.1021/ja028617z

  日期：2003.2.1

  The first radical intermediate in the thiourethane-mediated deoxygenation of an alcohol (Barton-McCombie reaction) can participate in an exo-hex-5-enyl- or exo-hept-6-enyl-type radical cyclization when a suitable radical acceptor (e.g., alpha,beta-unsaturated ester, oxime ether, or hydrazone) is appropriately placed. Carbohydrate-derived imidazolyl and triazolyl thiourethanes with such acceptors, upon addition to excess of a good hydride donor (reverse addition), undergo efficient cyclization reactions to give N-heterocyclic furanosides, and, surprisingly even N-pyranosides. Depending on the acceptor, glycosides with either a C(2)()-amino or a C(2)()-carbon substituent are formed.
• Efficient Syntheses of (S)-4-Hydroxy-2-pyrrolidinone Derivatives
  作者：Osamu Kanno、Masao Miyauchi、Isao Kawamoto

  DOI：10.3987/com-99-8689

  日期：——

  Efficient syntheses of (S)-4-hydroxy-2-pyrrolidinone ((S)-2) and (R)-4-acetylthio-2-pyrrolidinone (5), which are key intermediates of oral carbapenem CS-834, were studied. The most efficient route to (S)-2 from (S)-3-hydroxybutyrolactone (8) was accomplished in high yield via (S)-N-allyl-3-(1-ethoxy)ethoxy-4-hydroxybutyramide (14).
• Development of Noviomimetics as C-Terminal Hsp90 Inhibitors
  作者：Mercy Anyika、Mason McMullen、Leah K. Forsberg、Rick T. Dobrowsky、Brian S. J. Blagg

  DOI：10.1021/acsmedchemlett.5b00331

  日期：2016.1.14

  KU-32 and KU-596 are novobiocin-derived, C terminal heat shock protein 90 (Hsp90) modulators that induce Hsp70 levels and manifest neuroprotective activity. However, the synthetically complex noviose sugar requires 10 steps to prepare, which makes translational development difficult. In this study, we developed a series of "noviomimetic" analogues of KU-596, which contain noviose surrogates that can be easily prepared, while maintaining the ability to induce Hsp70 levels. Both sugar and sugar analogues were designed, synthesized, and evaluated in a luciferase reporter assay, which identified compound 37, a benzyl containing noviomimetic, as the most potent inducer of Hsp70.
• Yamada, Haruo; Sugiyama, Hajime; Kajiwara, Masahiro, Heterocycles, 1987, vol. 26, # 11, p. 2841 - 2844
  作者：Yamada, Haruo、Sugiyama, Hajime、Kajiwara, Masahiro

  DOI：——

  日期：——