(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpent-4-enoic acid | 519176-53-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpent-4-enoic acid
• CAS: 519176-53-5
• 化学式: C₁₂H₂₄O₃Si
• 分子量: 244.406
• InChiKey: CUUHPUODWBYKRS-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpent-4-enoic acid 在 叠氮磷酸二苯酯 、 氢氟酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 (3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-4,6,12-Trihydroxy-3,5,7,9,11,13-hexamethyl-14-vinyl-oxacyclotetradecane-2,10-dione
  参考文献：
  名称：

  Precursor directed biosynthesis of novel 6-deoxyerythronolide B analogs containing non-natural oxygen substituents and reactive functionalities

  摘要：

  Feeding of synthetic precursors to a blocked mutant of 6-deoxyerythronolide B synthase (DEBS) [1] led to production of novel 6-deoxyerythronolide B analogs in vivo containing additional non-natural oxygen substituents as well as additional reactive groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02507-6
• 作为产物：
  描述：

  <4S,3(2S,3R)>-4-benzyl-3-(3-hydroxy-2-methyl-4-pentenoyl)-2-oxazolidinone 在 lithium hydroxide 、 双氧水 、 N,N-二异丙基乙胺 、 sodium sulfite 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methylpent-4-enoic acid
  参考文献：
  名称：

  Precursor directed biosynthesis of novel 6-deoxyerythronolide B analogs containing non-natural oxygen substituents and reactive functionalities

  摘要：

  Feeding of synthetic precursors to a blocked mutant of 6-deoxyerythronolide B synthase (DEBS) [1] led to production of novel 6-deoxyerythronolide B analogs in vivo containing additional non-natural oxygen substituents as well as additional reactive groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02507-6

文献信息

• Stereocontrolled Synthesis of the Highly Functionalized Core Structure of Aurisides by Ring-Closing Metathesis
  作者：Emmanuel Bourcet、Fabienne Fache、Olivier Piva

  DOI：10.1002/ejoc.201000331

  日期：2010.7

  Two approaches based on the ring-closing metathesis reaction have been explored for the synthesis of the core structure of the marine natural products, the aurisides. The second approach, accomplished in a stereocontrolled manner, used both a Brown's allylation and an Evans' aldolisation, and finally a transannular ketalization to deliver a highly functionalized auriside analogue.

  已经探索了两种基于闭环复分解反应的方法来合成海洋天然产物金苷的核心结构。第二种方法以立体控制的方式完成，使用布朗烯丙基化和埃文斯醛醇化，最后使用跨环缩酮化来提供高度功能化的金苷类似物。
• Precursor directed biosynthesis of novel 6-deoxyerythronolide B analogs containing non-natural oxygen substituents and reactive functionalities
  作者：Daniel Hunziker、Nicholas Wu、Kenji Kenoshita、David E. Cane、Chaitan Khosla

  DOI：10.1016/s0040-4039(98)02507-6

  日期：1999.1

  Feeding of synthetic precursors to a blocked mutant of 6-deoxyerythronolide B synthase (DEBS) [1] led to production of novel 6-deoxyerythronolide B analogs in vivo containing additional non-natural oxygen substituents as well as additional reactive groups. (C) 1999 Elsevier Science Ltd. All rights reserved.