(S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-1,4-dioxaspiro[4.5]decan-2-one | 632357-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-1,4-dioxaspiro[4.5]decan-2-one
• 英文别名: (2S)-2-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1,4-dioxaspiro[4.5]decan-3-one
• CAS: 632357-45-0
• 化学式: C₁₆H₃₀O₄Si
• 分子量: 314.497
• InChiKey: RQQBAGHCNMTJCI-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-1,4-dioxaspiro[4.5]decan-2-one 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-butyric acid 5-methyl-2-methylene-hexyl ester
  参考文献：
  名称：

  Lasonolide A:  Structural Revision and Synthesis of the Unnatural (−)-Enantiomer

  摘要：

  Total synthesis of the unnatural (-)-enantiomer of lasonolide A was achieved starting from ethyl l-malate. The two tetrahydropyranyl fragments were prepared stereoselectively via radical cyclization reactions of beta-alkoxyacrylates. The full structure of natural lasonolide A was determined unequivocally.

  DOI：

  10.1021/ja017265d
• 作为产物：
  描述：

  1,4-二氧杂螺[4.5]癸烷-2-乙酸,3-羰基-,(2S)- 在 咪唑 、 硼酸三甲酯 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-1,4-dioxaspiro[4.5]decan-2-one
  参考文献：
  名称：

  Lasonolide A:  Structural Revision and Total Synthesis

  摘要：

  The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of beta-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantiomers of a revised structure featuring 17E,25Z double bonds were synthesized, and the (-)-isomer was found to be the biologically active enantiomer.

  DOI：

  10.1021/jo034930n

文献信息

• Synthesis of Enantiomerically Pure 2,5-Disubstituted 3-Oxygenated Tetrahydrofurans
  作者：Generosa Gómez、Yagamare Fall、Carla Álvarez、Manuel Pérez、Andrea Zúñiga

  DOI：10.1055/s-0030-1258263

  日期：2010.11

  The synthesis of enantiomerically pure 2,5-disubstituted 3-oxygenated tetrahydrofurans has been achieved from cheap and commercially available l-malic acid. This method was used to prepare an advanced intermediate toward CMI-977, a promising candidate for the treatment of chronic asthma. furan - tetrahydrofuran - singlet oxygen - butenolide - oxacycles­ - natural products

  对映体纯的2，5-二取代的3-氧化的四氢呋喃的合成已经由廉价的和可商购的1-苹果酸实现。该方法用于制备针对CMI-977的高级中间体，CMI-977是治疗慢性哮喘的有前途的候选药物。 呋喃-四氢呋喃-单线态氧-丁烯内酯-氧环化合物-天然产物
• Lasonolide A:  Structural Revision and Synthesis of the Unnatural (−)-Enantiomer
  作者：Eun Lee、Ho Young Song、Jung Won Kang、Dae-Shik Kim、Cheol-Kyu Jung、Jung Min Joo

  DOI：10.1021/ja017265d

  日期：2002.1.1

  Total synthesis of the unnatural (-)-enantiomer of lasonolide A was achieved starting from ethyl l-malate. The two tetrahydropyranyl fragments were prepared stereoselectively via radical cyclization reactions of beta-alkoxyacrylates. The full structure of natural lasonolide A was determined unequivocally.
• Lasonolide A:  Structural Revision and Total Synthesis
  作者：Ho Young Song、Jung Min Joo、Jung Won Kang、Dae-Shik Kim、Cheol-Kyu Jung、Hyo Shin Kwak、Jin Hyun Park、Eun Lee、Chang Yong Hong、ShinWu Jeong、Kiwan Jeon、Ji Hyun Park

  DOI：10.1021/jo034930n

  日期：2003.10.1

  The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of beta-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantiomers of a revised structure featuring 17E,25Z double bonds were synthesized, and the (-)-isomer was found to be the biologically active enantiomer.