(4S,5S)-4,5-Bis-[(R)-1-benzyloxy-2-((S)-toluene-4-sulfinyl)-ethyl]-2,2-dimethyl-[1,3]dioxolane | 219562-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5S)-4,5-Bis-[(R)-1-benzyloxy-2-((S)-toluene-4-sulfinyl)-ethyl]-2,2-dimethyl-[1,3]dioxolane
• 英文别名: (4S,5S)-2,2-dimethyl-4,5-bis[(1R)-2-[(S)-(4-methylphenyl)sulfinyl]-1-phenylmethoxyethyl]-1,3-dioxolane
• CAS: 219562-06-8
• 化学式: C₃₇H₄₂O₆S₂
• 分子量: 646.869
• InChiKey: RRPWCTIUVXXTHK-DXSKTLBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4,5-Bis-[(R)-1-benzyloxy-2-((S)-toluene-4-sulfinyl)-ethyl]-2,2-dimethyl-[1,3]dioxolane 在 2,4,6-三甲基吡啶 、 sodium tetrahydroborate 、 samarium diiodide 、 草酰氯 、 N,N-二异丙基乙胺 、 三氟乙酸酐 作用下， 反应 17.5h， 生成 (+/-)-1,4-di-O-benzyl-5,6-O-isopropylidine-myo-inositol
  参考文献：
  名称：

  Enantioselective Approach to Polyhydroxylated Compounds Using Chiral Sulfoxides:  Synthesis of Enantiomerically Pure myo-Inositol and Pyrrolidine Derivatives

  摘要：

  A short enantioselective synthesis of the biologically important myo-inositol derivative I and the pyrrolidine derivative II is described. The molecule 3, a diketo disulfoxide readily made from tartaric acid, is the key intermediate. The sulfinyl group controlled completely the very high stereoselection observed.

  DOI：

  10.1021/jo9811569
• 作为产物：
  描述：

  (S)-(-)-甲基对甲苯亚砜 在 四丁基碘化铵 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (4S,5S)-4,5-Bis-[(R)-1-benzyloxy-2-((S)-toluene-4-sulfinyl)-ethyl]-2,2-dimethyl-[1,3]dioxolane
  参考文献：
  名称：

  Enantioselective Approach to Polyhydroxylated Compounds Using Chiral Sulfoxides:  Synthesis of Enantiomerically Pure myo-Inositol and Pyrrolidine Derivatives

  摘要：

  A short enantioselective synthesis of the biologically important myo-inositol derivative I and the pyrrolidine derivative II is described. The molecule 3, a diketo disulfoxide readily made from tartaric acid, is the key intermediate. The sulfinyl group controlled completely the very high stereoselection observed.

  DOI：

  10.1021/jo9811569

文献信息

• Enantioselective Approach to Polyhydroxylated Compounds Using Chiral Sulfoxides:  Synthesis of Enantiomerically Pure <i>myo</i>-Inositol and Pyrrolidine Derivatives
  作者：Françoise Colobert、Amélia Tito、Noureddine Khiar、Donatienne Denni、Maria Angeles Medina、Manuel Martin-Lomas、José-Luis Garcia Ruano、Guy Solladié

  DOI：10.1021/jo9811569

  日期：1998.11.1

  A short enantioselective synthesis of the biologically important myo-inositol derivative I and the pyrrolidine derivative II is described. The molecule 3, a diketo disulfoxide readily made from tartaric acid, is the key intermediate. The sulfinyl group controlled completely the very high stereoselection observed.