(2S)-2-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-2H-furan-5-one | 149099-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2S)-2-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-2H-furan-5-one
• CAS: 149099-20-7
• 化学式: C₂₅H₃₀O₄Si
• 分子量: 422.596
• InChiKey: IDLKYLJIEJUWFD-VJBMBRPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (2S)-2-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-2H-furan-5-one 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 二异丁基氢化铝 、 三苯基膦 、 苯甲酸 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 26.5h， 生成 methyl (6R)-6-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-6-hydroxyhexanoate
  参考文献：
  名称：

  Stereocontrolled Total Synthesis of an Annonacin A-Type Acetogenin:  Pseudoannonacin A?

  摘要：

  A stereocontrolled first total synthesis of a diastereomer of the presumed mono-tetrahydrofuran type acetogenin annonacin A, starting with enantiomerically pure precursors, is described. The absolute stereochemistry of the C-15-C-20 segment corresponding to the tetrahydrofuran ring of the natural product was secured by X-ray crystal structure analysis of an advanced intermediate. The synthetic product (a mixture of epimers at C-10) had spectroscopic data identical to that of the natural product, but a different optical rotation.

  DOI：

  10.1021/jo9713621
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 4-二甲氨基吡啶 、 TEA 、 三氟化硼乙醚 、 乙酸酐 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (2S)-2-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-2H-furan-5-one
  参考文献：
  名称：

  Stereocontrolled Total Synthesis of an Annonacin A-Type Acetogenin:  Pseudoannonacin A?

  摘要：

  A stereocontrolled first total synthesis of a diastereomer of the presumed mono-tetrahydrofuran type acetogenin annonacin A, starting with enantiomerically pure precursors, is described. The absolute stereochemistry of the C-15-C-20 segment corresponding to the tetrahydrofuran ring of the natural product was secured by X-ray crystal structure analysis of an advanced intermediate. The synthetic product (a mixture of epimers at C-10) had spectroscopic data identical to that of the natural product, but a different optical rotation.

  DOI：

  10.1021/jo9713621

文献信息

• Tetrahydrofuran-podands, stereoselective synthesis of trans-2,5-oligo-tetrahydrofurans
  作者：Ulrich Koert、Matthias Stein、Klaus Harms

  DOI：10.1016/s0040-4039(00)77598-8

  日期：1993.4

  Enantiomerically pure THF-podands 1 were synthesized along a linear route starting from lactone 3. A high degree of stereochemical control was achieved by chelation controlled addition of the functionalized Grignard reagent 7 to α -alkoxy-aldehydes of type 6.

  对映体纯的THF-Podands 1从内酯3开始沿线性路线合成。高度立体化学控制是通过将官能化的格氏试剂7螯合控制地添加到6型α-烷氧基-醛中来实现的。
• Stereocontrolled Total Synthesis of an Annonacin A-Type Acetogenin:  Pseudoannonacin A?
  作者：Stephen Hanessian、Teresa Abad Grillo

  DOI：10.1021/jo9713621

  日期：1998.2.1

  A stereocontrolled first total synthesis of a diastereomer of the presumed mono-tetrahydrofuran type acetogenin annonacin A, starting with enantiomerically pure precursors, is described. The absolute stereochemistry of the C-15-C-20 segment corresponding to the tetrahydrofuran ring of the natural product was secured by X-ray crystal structure analysis of an advanced intermediate. The synthetic product (a mixture of epimers at C-10) had spectroscopic data identical to that of the natural product, but a different optical rotation.