(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid tert-butyl ester | 269715-76-6

• 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)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid tert-butyl ester
• 英文别名: tert-butyl (3S)-4-[tert-butyl(dimethyl)silyl]oxy-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 269715-76-6
• 化学式: C₂₂H₃₇NO₅Si
• 分子量: 423.625
• InChiKey: PUUBWNYPIGEFRS-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid tert-butyl ester 、 碘甲烷 在 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到(2R,3S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of a tricyclic guanidinium model of cylindrospermopsin

  摘要：

  An 11-step enantioselective synthesis of the A-ring of cylindrospermopsin is described using an intramolecular conjugate addition as the key step to forming the piperidine ring. Further elaboration generates a tricyclic guanidine via a sequential double displacement strategy as a model for the cylindrospermopsin guanidinium core. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02348-5
• 作为产物：
  描述：

  N-苄氧羰基-L-天冬氨酸4-叔丁酯1-(N-琥珀酰亚胺)酯 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of a tricyclic guanidinium model of cylindrospermopsin

  摘要：

  An 11-step enantioselective synthesis of the A-ring of cylindrospermopsin is described using an intramolecular conjugate addition as the key step to forming the piperidine ring. Further elaboration generates a tricyclic guanidine via a sequential double displacement strategy as a model for the cylindrospermopsin guanidinium core. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02348-5

文献信息

• Stereoselective synthesis of a tricyclic guanidinium model of cylindrospermopsin
  作者：Indrawan J. McAlpine、Robert W. Armstrong

  DOI：10.1016/s0040-4039(99)02348-5

  日期：2000.3

  An 11-step enantioselective synthesis of the A-ring of cylindrospermopsin is described using an intramolecular conjugate addition as the key step to forming the piperidine ring. Further elaboration generates a tricyclic guanidine via a sequential double displacement strategy as a model for the cylindrospermopsin guanidinium core. (C) 2000 Elsevier Science Ltd. All rights reserved.