(1S,2S,3S,4S)-5-bromo-1,2:3,4-di-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol | 154097-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,4S)-5-bromo-1,2:3,4-di-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol
• 英文别名: 1,2:3,4-di-O-isopropylidene-5-bromoconduritol D；(3aS,5aS,8aS,8bS)-4-bromo-2,2,7,7-tetramethyl-3a,5a,8a,8b-tetrahydro-[1,3]dioxolo[4,5-g][1,3]benzodioxole
• CAS: 154097-68-4
• 化学式: C₁₂H₁₇BrO₄
• 分子量: 305.169
• InChiKey: KRIDHVLBULQSCX-QCLAVDOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4S)-5-bromo-1,2:3,4-di-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.0h， 以98%的产率得到5-bromocoduritol D
  参考文献：
  名称：

  Carless, Howard A. J.; Busia, Kofi; Dove, Yvonne, Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2505 - 2506

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 5-bromocoduritol D 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 0.75h， 以1.2 g的产率得到(1S,2S,3S,4S)-5-bromo-1,2:3,4-di-O-isopropylidenecyclohex-5-ene-1,2,3,4-tetraol
  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

• Donohoe, Timothy J.; Moore, Peter R.; Beddoes, Roy L., Journal of the Chemical Society. Perkin transactions I, 1997, # 1, p. 43 - 52
  作者：Donohoe, Timothy J.、Moore, Peter R.、Beddoes, Roy L.

  DOI：——

  日期：——
• 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.
• Carless, Howard A. J.; Busia, Kofi; Dove, Yvonne, Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2505 - 2506
  作者：Carless, Howard A. J.、Busia, Kofi、Dove, Yvonne、Malik, Shahnaz S.

  DOI：——

  日期：——