(3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester | 865853-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
• 英文别名: 2-trimethylsilylethyl (3R,4S)-4-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-3-ethenylpiperidine-1-carboxylate
• CAS: 865853-22-1
• 化学式: C₃₁H₄₇NO₃Si₂
• 分子量: 537.89
• InChiKey: DYMHEYPZYMTEDA-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.55
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester 在 盐酸 、 AD-mix-β 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-trimethylsilylethyl (3R,4S)-4-[(2R,3R)-2,3-dihydroxy-3-(6-methoxyquinolin-4-yl)propyl]-3-ethenylpiperidine-1-carboxylate
  参考文献：
  名称：

  Improved synthesis of quinine alkaloids with the Teoc protective group

  摘要：

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.171
• 作为产物：
  描述：

  2-trimethylsilylethyl (3R,4S)-4-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-3-[2-(2,2-dimethylpropanoyloxy)ethyl]piperidine-1-carboxylate 在 2-硝基苯基丝氰酸酯 、 三丁基膦 、 sodium hydride 作用下， 以 乙醇 为溶剂， 生成 (3R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Improved synthesis of quinine alkaloids with the Teoc protective group

  摘要：

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.171

文献信息

• Improved synthesis of quinine alkaloids with the Teoc protective group
  作者：Junji Igarashi、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2005.06.171

  日期：2005.9

  TeocCl (Teoc: C(=O)O(CH2)(2)TMS) generated in situ was conveniently used for trans-protection of the N-Bn piperidine intermediate to N-Teoc piperidine. Later, deprotection of the Teoc group and the subsequent quinuclidine ring formation was achieved with CsF in a domino fashion to afford the quinine alkaloids. (c) 2005 Elsevier Ltd. All rights reserved.