(1S,2S,3S)-3-[tert-butyl(dimethyl)silyl]cyclohexane-4-ene-1,2-diol | 256942-68-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,2S,3S)-3-[tert-butyl(dimethyl)silyl]cyclohexane-4-ene-1,2-diol
• 英文别名: (1S,2S,3S)-3-[tert-butyl(dimethyl)silyl]cyclohex-4-ene-1,2-diol
• CAS: 256942-68-4
• 化学式: C₁₂H₂₄O₂Si
• 分子量: 228.407
• InChiKey: IZNSJPFJELPRFX-DCAQKATOSA-N

物化性质

• 沸点：
  289.9±40.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S)-3-[tert-butyl(dimethyl)silyl]cyclohexane-4-ene-1,2-diol 在 diethylzinc 、 sodium hydride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 34.0h， 生成 ((1R,2S,3S,4S,6R)-3,4-Bis-benzyloxy-bicyclo[4.1.0]hept-2-yl)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Synthesis of pseudo-sugars based on desymmetrization of dienylsilanes

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(97)10388-4
• 作为产物：
  描述：

  二甲基苯基(叔丁基)硅烷 在 potassium dioxotetrahydroxoosmate(VI) 、 chiral hydroquinone-2,5-diphenyl-4,6-pyrimidinediyl ether 、 氨 、 lithium 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 14.5h， 生成 (1S,2S,3S)-3-[tert-butyl(dimethyl)silyl]cyclohexane-4-ene-1,2-diol
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Fluorination process
  申请人：Gouverneur Veronique

  公开号：US20070142632A1

  公开（公告）日：2007-06-21

  Compounds of formula (II), (IIIa) or (IIIb) (variables are described in the specification) are prepared by fluorination of β,γ-unsaturated alkyl silanes. These compounds are useful as building blocks in the pharmaceutical industry.

  根据说明书中描述的变量，通过对β,γ-不饱和烷基硅烷进行氟化制备出式（II）、（IIIa）或（IIIb）的化合物。这些化合物在制药工业中作为构建模块非常有用。
• Sequential Desymmetrization–Fluorination: Enantioselective Synthesis of Fluorinated Cyclitols
  作者：Sophie Purser、Barbara Odell、Timothy D. W. Claridge、Peter R. Moore、Véronique Gouverneur

  DOI：10.1002/chem.200600861

  日期：2006.12.13

  An asymmetric synthesis of enantioenriched, highly functionalized fluorinated carbocycles has been developed based on an enantioselective Sharpless dihydroxylation of cyclohexadienylsilanes, combined with a diastereoselective electrophilic fluorodesilylation. Several parameters define the level of diastereocontrol for the fluorination step. These include the relative stereochemistry of the starting

  基于环己二烯基硅烷的对映选择性Sharpless二羟基化结合非对映选择性亲电氟代甲硅烷基化，已开发出对映富集的，高度官能化的氟化碳环的不对称合成。几个参数定义了氟化步骤的非对映控制水平。这些包括起始的内环烯丙基硅烷的相对立体化学和反应物的结构特征。如对于S（E）2′机理所预期的那样，氟脱甲硅烷基化以双键的干净转位发生，其中亲电子氟化剂的攻击优先于甲硅烷基而发生。对于氟化步骤，对于单环抗，顺式苄基保护的前体和顺式，顺式起始的烯丙基硅烷，观察到最佳的选择性。
• 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.