(R)-N-[(R)-1-(methyldiphenylsilyl)butyl]-2-methyl-2-propanesulfinamide

• 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: (R)-N-[(R)-1-(methyldiphenylsilyl)butyl]-2-methyl-2-propanesulfinamide
• 英文别名: (S(R))-N-[(R)-1-(methyldiphenylsilyl)butyl]-2-methyl-2-propanesulfinamide；(R)-2-methyl-N-[(1R)-1-[methyl(diphenyl)silyl]butyl]propane-2-sulfinamide
• 化学式: C₂₁H₃₁NOSSi
• 分子量: 373.635
• InChiKey: YBIZRGRLZHSGJS-HYBUGGRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  48.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯甲基硅烷 、 (R_S,E)-N-butylidene-2-methylpropane-2-sulfinamide 在 三甲基氯硅烷 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以86%的产率得到(R)-N-[(R)-1-(methyldiphenylsilyl)butyl]-2-methyl-2-propanesulfinamide
  参考文献：
  名称：

  Nielsen, Lone; Skrydstrup, Troels, Journal of the American Chemical Society, 2008, vol. 130, p. 13145 - 13151

  摘要：

  DOI：

文献信息

• Stereocontrolled Synthesis of Methyl Silanediol Peptide Mimics
  作者：Lone Nielsen、Karl B. Lindsay、Jesper Faber、Niels Christian Nielsen、Troels Skrydstrup

  DOI：10.1021/jo701907d

  日期：2007.12.1

  The treatment of chiral sulfinimines with (methyldiphenylsilyl)lithium gives alpha-(methyldiphenylsilyl)sulfinamides with excellent diastereoselectivity, and in good yield. The presence of alpha-protons on the imines is also well tolerated. The sulfinamide auxiliary is easily removed via treatment with methanolic HCl and the resulting amine extended into peptide chains accordingly. The diphenylsilyl moiety is a resilient protecting group for the corresponding silanediol, which can be unmasked via treatment with TfOH, followed by aqueous hydrolysis. The crude silanediol may be isolated and purified as its corresponding bis-TMS siloxane via protection with TMSCI, and converted back to the desired silanediol via hydrolysis with aqueous KOH. Efforts to apply this approach to biologically relevant silanediol peptide mimics, with a view to protease inhibition, are described.
• Nielsen, Lone; Skrydstrup, Troels, Journal of the American Chemical Society, 2008, vol. 130, p. 13145 - 13151
  作者：Nielsen, Lone、Skrydstrup, Troels

  DOI：——

  日期：——