(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one | 918310-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one
• CAS: 918310-84-6
• 化学式: C₁₉H₂₅NO₃Si
• 分子量: 343.498
• InChiKey: OVRULMORYPYWSS-WBVHZDCISA-N

物化性质

• 沸点：
  453.0±28.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 锂硼氢 、 pyridine-SO3 complex 、 水 、 碘 、 叔丁基锂 、 氟化氢吡啶 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 正戊烷 为溶剂， 反应 25.24h， 生成 (2S,3R,5R)-3-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-5-methyl-8-(trimethylsilyl)oct-7-ynal
  参考文献：
  名称：

  Antibodies with Broad Specificity to Azaspiracids by Use of Synthetic Haptens

  摘要：

  The development of general, sensitive, portable, and quantitative assays for the azaspiracid (AZA) class of marine toxins is urgently needed. Use of a synthetic hapten containing rings F-I of AZA to generate antibodies that cross-react with the AZAs via their common C28-C40 domain and use of these antibodies in ELISA and immunoaffinity columns are reported. This approach has many advantages over using intact azaspiracids (AZAs) derived from environmental samples or total synthesis as haptens for antibody development. A derivative of the levorotatory C28-C40 azaspiracid domain (1) was synthesized efficiently using a one-pot Staudinger reduction/intramolecular aza-Wittig reaction-imine capture sequence to form the H-I ring spiroaminal and a double intramolecluar hetero-Michael addition to assemble the F-G ring ketal. Conjugation of the hapten 1 to cBSA and immunization in sheep generated antibodies that recognized and bound to ovalbumin-conjugated 1 in the absence of AZA1. This binding was inhibited by 1 in a concentration-dependent manner. A mixture of AZA1, AZA2, AZA3, and AZA6 caused a degree of inhibition of antibody binding consistent with its total AZA content, rather than just its content of AZA1. This result suggests that the antibodies also have a similar affinity for AZA2, AZA3, and AZA6 as they do for AZA1 and that such antibodies are suitable for analysis of AZAs in shellfish samples.

  DOI：

  10.1021/ja066971h
• 作为产物：
  描述：

  3-iodo-1-propynyl(trimethyl)silane 、 (S)-4-苄基-3-丙酰基-2-噁唑烷酮 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以85%的产率得到(S)-4-benzyl-3-((R)-2-methyl-5-(trimethylsilyl)pent-4-ynoyl)oxazolidin-2-one
  参考文献：
  名称：

  Antibodies with Broad Specificity to Azaspiracids by Use of Synthetic Haptens

  摘要：

  The development of general, sensitive, portable, and quantitative assays for the azaspiracid (AZA) class of marine toxins is urgently needed. Use of a synthetic hapten containing rings F-I of AZA to generate antibodies that cross-react with the AZAs via their common C28-C40 domain and use of these antibodies in ELISA and immunoaffinity columns are reported. This approach has many advantages over using intact azaspiracids (AZAs) derived from environmental samples or total synthesis as haptens for antibody development. A derivative of the levorotatory C28-C40 azaspiracid domain (1) was synthesized efficiently using a one-pot Staudinger reduction/intramolecular aza-Wittig reaction-imine capture sequence to form the H-I ring spiroaminal and a double intramolecluar hetero-Michael addition to assemble the F-G ring ketal. Conjugation of the hapten 1 to cBSA and immunization in sheep generated antibodies that recognized and bound to ovalbumin-conjugated 1 in the absence of AZA1. This binding was inhibited by 1 in a concentration-dependent manner. A mixture of AZA1, AZA2, AZA3, and AZA6 caused a degree of inhibition of antibody binding consistent with its total AZA content, rather than just its content of AZA1. This result suggests that the antibodies also have a similar affinity for AZA2, AZA3, and AZA6 as they do for AZA1 and that such antibodies are suitable for analysis of AZAs in shellfish samples.

  DOI：

  10.1021/ja066971h

文献信息

• Synthesis and antiproliferative activity of new tonantzitlolone-derived diterpene derivatives
  作者：Torsten Busch、Gerald Dräger、Eike Kunst、Hannah Benson、Florenz Sasse、Karsten Siems、Andreas Kirschning

  DOI：10.1039/c6ob01697a

  日期：——

  The synthesis of the diterpene (+)-tonantzitlolone A and a series of derivatives is reported. The study includes the determination of their antiproliferative activities against selected cancer cell lines.

  报道了二萜（+）-tonantzitlolone A和一系列衍生物的合成。该研究包括确定它们对所选癌细胞系的抗增殖活性。