(3aR,4S,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxol-4-ol | 200707-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxol-4-ol
• CAS: 200707-80-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: UJHCCDZQVAXYRA-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxol-4-ol 在 草酰氯 、 叔丁基锂 、 二甲基亚砜 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 2.67h， 生成 (3aS,5R,6R,7aS)-6-[(1E,3E)-hepta-1,3-dienyl]-5-(hydroxymethyl)-2,2-dimethyl-5,6,7,7a-tetrahydro-3aH-1,3-benzodioxol-4-one
  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 potassium fluoride 、 (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 、 双氧水 、 potassium carbonate 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 26.0h， 生成 (3aR,4S,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydro-1,3-benzodioxol-4-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

• Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes
  作者：Rémy Angelaud、Yannick Landais

  DOI：10.1016/s0040-4039(97)10388-4

  日期：1997.12

  A synthesis of pseudo-sugars using the desymmetrization of a dienylsilane, followed by a stereocontrolled introduction of the hydroxymethyl group at C5. is described. The CH2OH group at C5 was elaborated using either a regioselective cyclopropane-ring opening or a [2,3]-Wittig rearrangement. (C) 1997 Elsevier Science Ltd.
• 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
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  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.