methyl 3-((4R,5R)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-4,5-dihydrooxazol-5-yl)propanoate | 1018785-52-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-((4R,5R)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-4,5-dihydrooxazol-5-yl)propanoate
• 英文别名: methyl 3-[(4R,5R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-phenyl-4,5-dihydro-1,3-oxazol-5-yl]propanoate
• CAS: 1018785-52-8
• 化学式: C₂₀H₃₁NO₄Si
• 分子量: 377.556
• InChiKey: KLYOOJZZHUDMDF-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-((4R,5R)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-4,5-dihydrooxazol-5-yl)propanoate 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、482.64 kPa 条件下， 反应 72.0h， 以80%的产率得到(5R,6R)-6-((tert-butyldimethylsilyloxy)methyl)-5-hydroxypiperidin-2-one
  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：

  (E)-methyl 3-((4R,5R)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-4,5-dihydrooxazol-5-yl)acrylate 在 L-Selectride 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以86%的产率得到methyl 3-((4R,5R)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-4,5-dihydrooxazol-5-yl)propanoate
  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.