Carbamic acid,[(1S,2R)-2-cyano-1-(cyclohexylmethyl)-2-[(trimethylsilyl)oxy]ethyl]-,1,1-dimethylethyl ester | 117499-02-2

• 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: Carbamic acid,[(1S,2R)-2-cyano-1-(cyclohexylmethyl)-2-[(trimethylsilyl)oxy]ethyl]-,1,1-dimethylethyl ester
• 英文别名: ((S)-2-Cyano-1-cyclohexylmethyl-2-trimethylsilanyloxy-ethyl)-carbamic acid tert-butyl ester
• CAS: 117499-02-2；117499-03-3
• 化学式: C₁₈H₃₄N₂O₃Si
• 分子量: 354.565
• InChiKey: JMBGSPCBVIBIOP-VYRBHSGPSA-N

物化性质

• 沸点：
  434.9±40.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  71.35
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Carbamic acid,[(1S,2R)-2-cyano-1-(cyclohexylmethyl)-2-[(trimethylsilyl)oxy]ethyl]-,1,1-dimethylethyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane
  参考文献：
  名称：

  Potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme identified in rat lung

  摘要：

  Two structurally distinct series of potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme (ECE) activity identified in the rat lung have been developed. Pepstatin A, which potently inhibits the rat lung ECE, served as the basis for the first series. Alternatively, selected renin inhibitors containing the dihydroxyethylene moiety were shown to be inhibitors of rat lung activity. Subsequent modifications improved inhibition of the rat lung ECE while eliminating renin activity. Both series of ECE inhibitors demonstrated a range of selectivity over Cathepsin D. Water-solubilizing moieties were appended onto selected compounds to facilitate in vivo testing. Partial reduction of the pressor response to exogenously administered Big ET-1 was observed with selected rat lung ECE inhibitors.

  DOI：

  10.1021/jm00056a007
• 作为产物：
  描述：

  S-(-)-2-N-BOC-3-环己基-1-丙醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 zinc(II) iodide 作用下， 生成 Carbamic acid,[(1S,2R)-2-cyano-1-(cyclohexylmethyl)-2-[(trimethylsilyl)oxy]ethyl]-,1,1-dimethylethyl ester
  参考文献：
  名称：

  Potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme identified in rat lung

  摘要：

  Two structurally distinct series of potent and selective inhibitors of an aspartyl protease-like endothelin converting enzyme (ECE) activity identified in the rat lung have been developed. Pepstatin A, which potently inhibits the rat lung ECE, served as the basis for the first series. Alternatively, selected renin inhibitors containing the dihydroxyethylene moiety were shown to be inhibitors of rat lung activity. Subsequent modifications improved inhibition of the rat lung ECE while eliminating renin activity. Both series of ECE inhibitors demonstrated a range of selectivity over Cathepsin D. Water-solubilizing moieties were appended onto selected compounds to facilitate in vivo testing. Partial reduction of the pressor response to exogenously administered Big ET-1 was observed with selected rat lung ECE inhibitors.

  DOI：

  10.1021/jm00056a007

文献信息

• Unique Stereocontrol in Europium(III)-Catalyzed Cyanosilylation of Chiral α-Alkoxy and α-Amino Aldehydes
  作者：Jin-Hua Gu、Mikako Okamoto、Masahiro Terada、Koichi Mikami、Takeshi Nakai

  DOI：10.1246/cl.1992.1169

  日期：1992.7

  The Eu(III)-catalyzed cyanosilylations of chiral α-alkoxy and α-amino aldehydes are shown to exhibit syn diastereofacial selection, the degree increasing with an increase in steric bulk of the alkyl chain in the aldehydes. The mechanism of this catalytic process is discussed.

  研究表明，Eu(III)催化的手性α-烷氧基和α-氨基醛的氰硅化反应展现出了syn二面体选择性，且随着醛中烷基链空间位阻的增加，其选择性也增强。同时还讨论了这一催化过程的机理。
• A convenient stereoselective synthesis of 1,2,3-aminodiols from .alpha.-amino acids
  作者：Jay R. Luly、Chi Nung Hsiao、Nwe BaMaung、Jacob J. Plattner

  DOI：10.1021/jo00261a024

  日期：1988.12