(3'R,4S,4'S,5R,5'R)-4-benzyl-3-((5'-methyl-2',3'diphenylisoxazolidin-4'-yl)carbonyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone | 864072-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3'R,4S,4'S,5R,5'R)-4-benzyl-3-((5'-methyl-2',3'diphenylisoxazolidin-4'-yl)carbonyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
• 英文别名: (4S,5R)-4-benzyl-3-[(3R,4S,5R)-5-methyl-2,3-diphenyl-1,2-oxazolidine-4-carbonyl]-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1,3-oxazolidin-2-one
• CAS: 864072-74-2
• 化学式: C₃₅H₂₉F₁₃N₂O₄
• 分子量: 788.605
• InChiKey: QQPACJVYLCOAFD-ZGUHPQOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  54
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (3'R,4S,4'S,5R,5'R)-4-benzyl-3-((5'-methyl-2',3'diphenylisoxazolidin-4'-yl)carbonyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 、 异丙醇 在 titanium(IV) isopropylate 作用下， 以 甲苯 为溶剂， 以92%的产率得到(3R,4S,5R)-4-isoxazolidinecarboxylic acid, 5-methyl-2,3-diphenyl-, isopropyl ester
  参考文献：
  名称：

  Recyclable supports for stereoselective 1,3-dipolar cycloadditions: application of a fluorous oxazolidinone chiral auxiliary

  摘要：

  The utility of a new fluorous-supported chiral auxiliary was tested using a series of catalyzed and uncatalyzed 1,3-dipolar cycloaddition reactions with diphenylnitrone. The yields and selectivities of the cycloadducts compare favourably with those obtained using the conventional Evans-type auxiliaries, while purification was greatly assisted by using fluorous solid phase extraction. Following characterization, the cycloadducts were released from the auxiliaries by reductive cleavage. The auxiliary was readily refunctionalized and reused in subsequent cycloaddition reactions, with no deterioration of the observed yields or selectivities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.041
• 作为产物：
  描述：

  4-苄基-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟辛基)-1,3-恶唑烷-2-酮 在 magnesium(II) perchlorate 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (3'R,4S,4'S,5R,5'R)-4-benzyl-3-((5'-methyl-2',3'diphenylisoxazolidin-4'-yl)carbonyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone
  参考文献：
  名称：

  Recyclable supports for stereoselective 1,3-dipolar cycloadditions: application of a fluorous oxazolidinone chiral auxiliary

  摘要：

  The utility of a new fluorous-supported chiral auxiliary was tested using a series of catalyzed and uncatalyzed 1,3-dipolar cycloaddition reactions with diphenylnitrone. The yields and selectivities of the cycloadducts compare favourably with those obtained using the conventional Evans-type auxiliaries, while purification was greatly assisted by using fluorous solid phase extraction. Following characterization, the cycloadducts were released from the auxiliaries by reductive cleavage. The auxiliary was readily refunctionalized and reused in subsequent cycloaddition reactions, with no deterioration of the observed yields or selectivities. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.05.041

文献信息

• Recyclable supports for stereoselective 1,3-dipolar cycloadditions: application of a fluorous oxazolidinone chiral auxiliary
  作者：Jason E. Hein、Philip G. Hultin

  DOI：10.1016/j.tetasy.2005.05.041

  日期：2005.7

  The utility of a new fluorous-supported chiral auxiliary was tested using a series of catalyzed and uncatalyzed 1,3-dipolar cycloaddition reactions with diphenylnitrone. The yields and selectivities of the cycloadducts compare favourably with those obtained using the conventional Evans-type auxiliaries, while purification was greatly assisted by using fluorous solid phase extraction. Following characterization, the cycloadducts were released from the auxiliaries by reductive cleavage. The auxiliary was readily refunctionalized and reused in subsequent cycloaddition reactions, with no deterioration of the observed yields or selectivities. (c) 2005 Elsevier Ltd. All rights reserved.