(S)-(-)-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]carbamic acid tert-butyl ester | 336607-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(-)-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-(3,4-dimethoxyphenyl)propan-2-yl]carbamate
• CAS: 336607-94-4
• 化学式: C₃₂H₄₃NO₅Si
• 分子量: 549.783
• InChiKey: ZASINKJOYUXYHI-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(-)-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]carbamic acid tert-butyl ester 在 四丁基氟化铵 、 sodium acetate 、 乙酸酐 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 1-[(1R)-2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]tetrahydro-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Diastereoselective Intramolecular α-Amidoalkylation Reactions of l-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinolines

  摘要：

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).

  DOI：

  10.1021/jo051584w
• 作为产物：
  描述：

  3,4-二甲氧基-L-苯丙氨酸 在 lithium aluminium tetrahydride 作用下， 生成 (S)-(-)-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations

  摘要：

  Stereocontrolled N-acyliminium ion cyclisation of L-DOPA derived succinimide 5 has been investigated. Addition of organolithiums to chiral non-racemic 5 yields oxoamides, which are cyclised diastereoselectively upon treatment with BF3-OEt2, to afford 5,10b-trans pyrroloisoquinolones in moderate yields and high ee (99%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02319-4

文献信息

• Diastereoselective Intramolecular α-Amidoalkylation Reactions of <scp>l</scp>-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinolines
  作者：Eva García、Sonia Arrasate、Esther Lete、Nuria Sotomayor

  DOI：10.1021/jo051584w

  日期：2005.12.1

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).
• Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations
  作者：Eva Garcı́a、Sonia Arrasate、Ainhoa Ardeo、Esther Lete、Nuria Sotomayor

  DOI：10.1016/s0040-4039(00)02319-4

  日期：2001.2

  Stereocontrolled N-acyliminium ion cyclisation of L-DOPA derived succinimide 5 has been investigated. Addition of organolithiums to chiral non-racemic 5 yields oxoamides, which are cyclised diastereoselectively upon treatment with BF3-OEt2, to afford 5,10b-trans pyrroloisoquinolones in moderate yields and high ee (99%). (C) 2001 Elsevier Science Ltd. All rights reserved.