(1S,2S,3S)-3-[hydroxy(dimethyl)silyl]cyclohex-4-ene-1,2-diol | 914301-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S)-3-[hydroxy(dimethyl)silyl]cyclohex-4-ene-1,2-diol
• CAS: 914301-72-7
• 化学式: C₈H₁₆O₃Si
• 分子量: 188.299
• InChiKey: XUJNRYMWQDHLND-FXQIFTODSA-N

物化性质

• 沸点：
  292.0±40.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.24
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S)-3-[hydroxy(dimethyl)silyl]cyclohex-4-ene-1,2-diol 在 potassium fluoride 、 四氧化锇 、 双氧水 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 34.0h， 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
• 作为产物：
  描述：

  Cyclohexa-2,5-dienyl-dimethyl-silanol 在 (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan) 、 甲基磺酰胺 、 K₂OsO₂*2H₂O 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 12.0h， 生成 (1S,2S,3S)-3-[hydroxy(dimethyl)silyl]cyclohex-4-ene-1,2-diol
  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

• Landais, Yannick, Chimia, 1998, vol. 52, # 3, p. 104 - 111
  作者：Landais, Yannick

  DOI：——

  日期：——
• Desymmetrization of a Silyl-2,5-cyclohexadiene. Synthesis of (+)-Conduritol E and (−)-2-Deoxy-<i>allo</i>-inositol
  作者：Rémy Angelaud、Yannick Landais

  DOI：10.1021/jo960814r

  日期：1996.1.1