[(S)-1-((S)-1-Formyl-2-methyl-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester | 383129-47-3

• 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: [(S)-1-((S)-1-Formyl-2-methyl-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 383129-47-3
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: QCDLNALMEBTSSN-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-1-((S)-1-Formyl-2-methyl-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 在 4-甲基苯磺酸吡啶 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 {(S)-1-Benzyl-2-[(4S,5S)-5-(2-benzyl-allyl)-4-isopropyl-2,2-dimethyl-oxazolidin-3-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Allyltrichlorostannane additions to chiral dipeptide aldehydes

  摘要：

  The first examples of successful allylsilane additions to chiral dipeptide aldehydes are described. Treatment of allylsilanes with tin tetrachloride at room temperature affords allyltrichlorostarnnane intermediates that reacts with dipeptide aldehydes to give 1,2-syn-homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene dipeptide isosteres. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01502-7
• 作为产物：
  描述：

  (S)-2-Amino-N-methoxy-3,N-dimethyl-butyramide; hydrochloride 在 lithium aluminium tetrahydride 、 碳酸氢钠 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(S)-1-((S)-1-Formyl-2-methyl-propylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Allyltrichlorostannane additions to chiral dipeptide aldehydes

  摘要：

  The first examples of successful allylsilane additions to chiral dipeptide aldehydes are described. Treatment of allylsilanes with tin tetrachloride at room temperature affords allyltrichlorostarnnane intermediates that reacts with dipeptide aldehydes to give 1,2-syn-homoallylic alcohols, potential intermediates for the synthesis of hydroxyethylene dipeptide isosteres. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01502-7

文献信息

• Stereoselective synthesis of dienylamines: from amino acids to E-alkene dipeptide isosters
  作者：Gianna Reginato、Francesca Gaggini、Alessandro Mordini、Michela Valacchi

  DOI：10.1016/j.tet.2005.04.068

  日期：2005.7

  A stereoselective approach to dienylamines is described, starting from enantiomerically enriched stannylated allylamines, which are in turn derived from amino acids. Conveniently the procedure allows to introduce diversity at 1-,2- and 4- positions of the final compounds. Conversion to vinylstannane has been extended to dipeptido aldehydes. The possible elaboration of 4-methyl substituted dienylamines

  描述了一种对二烯基胺的立体选择方法，其始于对映异构体富集的甲锡烷基化烯丙胺，而后者又衍生自氨基酸。方便地，该方法允许在最终化合物的1-，2-和4-位上引入多样性。转化为乙烯基锡烷已扩展到二肽基醛。4-甲基取代的二烯基胺可能修饰为Boc-Gly-Ψ[（E）-CHCH]-（l，d）-Ala和Boc-Phe-Ψ[（E）-CHCH]-（l，d）-还显示了丙氨酸二肽等排物。