5,6-Anhydro-allo-inositol-diaceton-ketal | 744209-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 5,6-Anhydro-allo-inositol-diaceton-ketal
• 英文别名: O¹,O²;O³,O⁴-diisopropyliden-5,6-anhydro-allo-inositol；O¹,O²;O³,O⁴-Diisopropyliden-5,6-anhydro-allo-inosit；(1R,2S,4R,5S,9S,10R)-7,7,12,12-tetramethyl-3,6,8,11,13-pentaoxatetracyclo[8.3.0.02,4.05,9]tridecane
• CAS: 744209-88-9
• 化学式: C₁₂H₁₈O₅
• 分子量: 242.272
• InChiKey: IVJPXHHNHCGORL-UXOIPIPASA-N

物化性质

• 熔点：
  97-98 °C(Solv: ligroine (8032-32-4))
• 沸点：
  305.5±37.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-Anhydro-allo-inositol-diaceton-ketal 在 DOWEX 1X₈-200 resin 作用下， 以 水 为溶剂， 反应 24.0h， 以90%的产率得到epi-Inositol
  参考文献：
  名称：

  Concise chemoenzymatic synthesis of epi-inositol

  摘要：

  epi-Inositol was synthesized in six steps in 40% overall yield from a bacterial bromobenzene metabolite. The chemoenzymatic route involved toluene dioxygenase oxidation, substrate-directed catalytic osmylation, m-CPBA epoxidation, radical debromination, and Amberlite-catalized hydrolysis. The route described is amenable to scaleup and could allow access to cis-inositol, and deoxy derivatives of epi-inositol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.011
• 作为产物：
  描述：

  (1S,2R,4S,5R,9R,10S)-2-bromo-7,7,12,12-tetramethyl-3,6,8,11,13-pentaoxatetracyclo[8.3.0.02,4.05,9]tridecane 在 三正丁基氢锡 、 过氧化苯甲酰 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到5,6-Anhydro-allo-inositol-diaceton-ketal
  参考文献：
  名称：

  Concise chemoenzymatic synthesis of epi-inositol

  摘要：

  epi-Inositol was synthesized in six steps in 40% overall yield from a bacterial bromobenzene metabolite. The chemoenzymatic route involved toluene dioxygenase oxidation, substrate-directed catalytic osmylation, m-CPBA epoxidation, radical debromination, and Amberlite-catalized hydrolysis. The route described is amenable to scaleup and could allow access to cis-inositol, and deoxy derivatives of epi-inositol. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.04.011

文献信息

• 728. Cyclitols. Part VII. Anhydroinositols and the “epoxide migration.”
  作者：S. J. Angyal、P. T. Gilham

  DOI：10.1039/jr9570003691

  日期：——
• Nuclear Magnetic Resonance Spectrum of a Diastereomer of Quercitol (Deoxyinositol). Synthesis of allo-Quercitol and its 6-Chloro, 6-Bromo and 6-Iodo Derivatives^1,2
  作者：J. N. Shoolery、L. F. Johnson、Stanley Furuta、G. E. McCasland

  DOI：10.1021/ja01481a035

  日期：1961.10
• Application of Spin Decoupling and 100-Megacycle Spectra to Characterization of Carbohydrates. Novel Synthesis of a Cyclohexanetetrol^1,2
  作者：G. E. McCasland、Stanley Furuta、L. F. Johnson、J. N. Shoolery

  DOI：10.1021/jo01031a061

  日期：1964.8
• Concise chemoenzymatic synthesis of epi-inositol
  作者：Cecilia Vitelio、Ana Bellomo、Margarita Brovetto、Gustavo Seoane、David Gonzalez

  DOI：10.1016/j.carres.2004.04.011

  日期：2004.7

  epi-Inositol was synthesized in six steps in 40% overall yield from a bacterial bromobenzene metabolite. The chemoenzymatic route involved toluene dioxygenase oxidation, substrate-directed catalytic osmylation, m-CPBA epoxidation, radical debromination, and Amberlite-catalized hydrolysis. The route described is amenable to scaleup and could allow access to cis-inositol, and deoxy derivatives of epi-inositol. (C) 2004 Elsevier Ltd. All rights reserved.