(2R,3S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid tert-butyl ester | 269715-77-7

• 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: (2R,3S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S)-4-[tert-butyl(dimethyl)silyl]oxy-2-methyl-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 269715-77-7
• 化学式: C₂₃H₃₉NO₅Si
• 分子量: 437.652
• InChiKey: MMIQPRAIBKSZEF-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (2R,3S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid tert-butyl ester 在 palladium on activated charcoal 2,6-二甲基吡啶 、 三氟化硼乙醚 、 氢气 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 臭氧 、 三乙胺 、 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 生成 1-[(2R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methylpiperidin-2-yl]propan-2-one
  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：

  (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

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.