(5R)-5-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]oxolan-2-one | 149099-21-8

• 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: (5R)-5-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]oxolan-2-one
• CAS: 149099-21-8
• 化学式: C₂₅H₃₂O₄Si
• 分子量: 424.612
• InChiKey: KQCQVCJXACZTHY-AJSBUHFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  (5R)-5-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]oxolan-2-one 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 、 苯甲酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 20.0h， 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 palladium on activated charcoal 4-二甲氨基吡啶 、 TEA 、 三氟化硼乙醚 、 氢气 、 乙酸酐 、 二异丁基氢化铝 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， -78.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 (5R)-5-[(2S,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]oxolan-2-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

• 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.