(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 | 743444-60-2

• 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: (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
• CAS: 743444-60-2
• 化学式: C₁₂H₁₇BrO₅
• 分子量: 321.168
• InChiKey: HNRGPBQNUCJEJH-PEFUKATBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 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：

  (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
• 作为产物：
  描述：

  5-bromocoduritol D 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 丙酮 为溶剂， 反应 6.75h， 生成 (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
  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

• 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.