phenylmethyl ((S)-1-methyl-2-[((S)-{[(R)-2-methyl-1-(methyldiphenylsilyl)propyl]amino}carbonyl)pyrrolidin-1-yl]-2-oxoethyl)carbamate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenylmethyl ((S)-1-methyl-2-[((S)-{[(R)-2-methyl-1-(methyldiphenylsilyl)propyl]amino}carbonyl)pyrrolidin-1-yl]-2-oxoethyl)carbamate
• 英文别名: benzyl N-[(2S)-1-[(2S)-2-[[(1R)-2-methyl-1-[methyl(diphenyl)silyl]propyl]carbamoyl]pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate
• 化学式: C₃₃H₄₁N₃O₄Si
• 分子量: 571.792
• InChiKey: GOGXADKATNOCCD-ZITMISKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenylmethyl ((S)-1-methyl-2-[((S)-{[(R)-2-methyl-1-(methyldiphenylsilyl)propyl]amino}carbonyl)pyrrolidin-1-yl]-2-oxoethyl)carbamate 在 palladium on activated charcoal 、 palladium dichloride 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 (2S)-1-[(2S)-2-aminopropanoyl]-N-[(1R)-2-methyl-1-[methyl(diphenyl)silyl]propyl]pyrrolidine-2-carboxamide;hydrochloride
  参考文献：
  名称：

  Stereocontrolled Synthesis of Methyl Silanediol Peptide Mimics

  摘要：

  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.

  DOI：

  10.1021/jo701907d
• 作为产物：
  描述：

  (2S)-N-[(1R)-2-methyl-1-[methyl(diphenyl)silyl]propyl]pyrrolidine-2-carboxamide;2,2,2-trifluoroacetic acid 、 苄氧羰基-L-丙氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 以140 mg的产率得到phenylmethyl ((S)-1-methyl-2-[((S)-{[(R)-2-methyl-1-(methyldiphenylsilyl)propyl]amino}carbonyl)pyrrolidin-1-yl]-2-oxoethyl)carbamate
  参考文献：
  名称：

  Stereocontrolled Synthesis of Methyl Silanediol Peptide Mimics

  摘要：

  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.

  DOI：

  10.1021/jo701907d