(2R,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-3-hydroxypiperidine-1-carboxylate | 1018785-55-1

• 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: (2R,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-3-hydroxypiperidine-1-carboxylate
• 英文别名: tert-butyl (2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]piperidine-1-carboxylate
• CAS: 1018785-55-1
• 化学式: C₂₃H₄₉NO₄Si₂
• 分子量: 459.817
• InChiKey: PWSQTDGCHPNMMT-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-3-hydroxypiperidine-1-carboxylate 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以94%的产率得到(2R,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-3-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Stereoselective total synthesis of (2S,3R)-3-hydroxypipecolic acid

  摘要：

  A concise, stereocontrolled synthesis of (2S,3R)-3-hydroxypipecolic acid 1 is described. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0) and intramolecular cyclization by catalytic hydrogenation of an oxazoline. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.010
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (rac)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-hydroxypiperidine-1-carboxylate 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以95%的产率得到(2R,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-3-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Stereoselective total synthesis of (2S,3R)-3-hydroxypipecolic acid

  摘要：

  A concise, stereocontrolled synthesis of (2S,3R)-3-hydroxypipecolic acid 1 is described. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0) and intramolecular cyclization by catalytic hydrogenation of an oxazoline. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.010

文献信息

• Stereoselective total synthesis of (2S,3R)-3-hydroxypipecolic acid
  作者：Van-Thoai Pham、Jae-Eun Joo、Yong-Shou Tian、Yun-Sung Chung、Kee-Young Lee、Chang-Young Oh、Won-Hun Ham

  DOI：10.1016/j.tetasy.2008.01.010

  日期：2008.2

  A concise, stereocontrolled synthesis of (2S,3R)-3-hydroxypipecolic acid 1 is described. Key features involve diastereoselective oxazoline formation catalyzed by palladium(0) and intramolecular cyclization by catalytic hydrogenation of an oxazoline. (C) 2008 Elsevier Ltd. All rights reserved.