(S)-methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutanoate | 1426434-47-0

• 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)-methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutanoate
• 英文别名: methyl (2S)-2-[[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-(3,4-dimethoxyphenyl)ethyl]amino]-3-methylbutanoate
• CAS: 1426434-47-0
• 化学式: C₂₂H₃₉NO₅Si
• 分子量: 425.641
• InChiKey: VMMRMGBPEUUXES-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以77%的产率得到(S)-2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutan-1-ol
  参考文献：
  名称：

  An Approach to the Synthesis of Enantiopure Tetrahydroisoquinoline via a Key Asymmetric Ugi Reaction

  摘要：

  An approach to the synthesis of the multisubstituted tetrahydroisoquinoline featuring an asymmetric Ugi reaction of a-amino acid, aromatic aldehyde and an isocyanide has been developed. The promising utility of the strategy is demonstrated by a synthesis of an enantiopure functionalized 1,3-trans-tetrahydroiso-quinolin-4-ol from natural L-valine. The configuration of the two stereocenters at C-1 and C-4, generated in the Ugi reaction and Pomeranz-Fritsch-type cyclization separately, was controlled very well and determined by NMR studies.

  DOI：

  10.1055/s-0032-1317931
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 98.0h， 生成 (S)-methyl 2-((R)-2-(tert-butyldimethylsilyloxy)-1-(3,4-dimethoxyphenyl)ethylamino)-3-methylbutanoate
  参考文献：
  名称：

  An Approach to the Synthesis of Enantiopure Tetrahydroisoquinoline via a Key Asymmetric Ugi Reaction

  摘要：

  An approach to the synthesis of the multisubstituted tetrahydroisoquinoline featuring an asymmetric Ugi reaction of a-amino acid, aromatic aldehyde and an isocyanide has been developed. The promising utility of the strategy is demonstrated by a synthesis of an enantiopure functionalized 1,3-trans-tetrahydroiso-quinolin-4-ol from natural L-valine. The configuration of the two stereocenters at C-1 and C-4, generated in the Ugi reaction and Pomeranz-Fritsch-type cyclization separately, was controlled very well and determined by NMR studies.

  DOI：

  10.1055/s-0032-1317931