(1R,3R,7S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-ol | 257294-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3R,7S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-ol
• CAS: 257294-38-5
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: GZAUSEVVFGFLES-YIKMNZTOSA-N

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：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3R,7S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-ol 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1α,2α,3α,4β,5β)-pentahydroxycyclohexane
  参考文献：
  名称：

  Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics

  摘要：

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.

  DOI：

  10.1021/jo991225z
• 作为产物：
  描述：

  (3aS,4S,5S,6S,7aS)-4-(Methoxy-dimethyl-silanyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5,6-diol 在 potassium fluoride 、 双氧水 、 potassium hydrogencarbonate 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (1R,3R,7S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-ol
  参考文献：
  名称：

  Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics

  摘要：

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.

  DOI：

  10.1021/jo991225z

文献信息

• A unified and common intermediate strategy for the asymmetric total synthesis of 3-deoxy-neo-inositol and conduritol E
  作者：Amarendra Panda、Rayhan Gafur Biswas、Shantanu Pal

  DOI：10.1016/j.tetlet.2016.06.127

  日期：2016.8

  3-deoxy-neo-inositol and conduritol E starting from d-ribose via a common chiral cyclohexenol derivative. The focal attributes of the synthetic route include stereoselective Grignard reaction, Wittig olefination, ring closing metathesis (RCM), and cis dihydroxylation.

  对于对映体纯的3-脱氧-新肌醇和conduritol E，从d-核糖开始，通过常见的手性环己烯醇衍生物，已经概述了一种有效，简单且统一的合成方法。合成路线的重点属性包括立体选择性格氏反应，Wittig烯烃化，闭环复分解（RCM）和顺式二羟基化。