(3RS,6R)-6-(hydroxymethyl)-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one | 187851-99-6

• 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: (3RS,6R)-6-(hydroxymethyl)-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one
• 英文别名: (6R)-6-(hydroxymethyl)-3-phenylselanyloxan-2-one
• CAS: 187851-99-6
• 化学式: C₁₂H₁₄O₃Se
• 分子量: 285.201
• InChiKey: PYZUFHRHMXSNID-BFHBGLAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  (3RS,6R)-6-(hydroxymethyl)-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one 在 草酰氯 、 双氧水 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-6-Oxo-3,6-dihydro-2H-pyran-2-carbaldehyde
  参考文献：
  名称：

  Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)

  摘要：

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.

  DOI：

  10.1021/jo962166h
• 作为产物：
  描述：

  5-己烯酸 在 咪唑 、 (DHQD)2AQN 、 K₂OsO₂(OH)2 、 四丁基氟化铵 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 苯甲醚 、 三氟乙酸 、 potassium hexacyanoferrate(III) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 145.5h， 生成 (3RS,6R)-6-(hydroxymethyl)-3-(phenylselenyl)-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)

  摘要：

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.

  DOI：

  10.1021/jo962166h

文献信息

• Determination of the Relative and Absolute Stereochemistry of Fostriecin (CI-920)
  作者：Dale L. Boger、Masataka Hikota、Bryan M. Lewis

  DOI：10.1021/jo962166h

  日期：1997.3.1

  The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D H-1-H-1 NMR. NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.