(7aS)-6-hydroxy-1-oxo-3,3-bis(trifluoromethyl)-7,7a-dihydro-pyrrolo[1,2-c]oxazole-5-carboxylic acid ethyl ester | 193526-22-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (7aS)-6-hydroxy-1-oxo-3,3-bis(trifluoromethyl)-7,7a-dihydro-pyrrolo[1,2-c]oxazole-5-carboxylic acid ethyl ester
• 英文别名: ethyl (5S,6S,7aS)-6-hydroxy-1-oxo-3,3-bis(trifluoromethyl)-5,6,7,7a-tetrahydropyrrolo[1,2-c][1,3]oxazole-5-carboxylate
• CAS: 193526-22-6
• 化学式: C₁₁H₁₁F₆NO₅
• 分子量: 351.202
• InChiKey: BECXZDWBDQLDRJ-ZLUOBGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (7aS)-6-hydroxy-1-oxo-3,3-bis(trifluoromethyl)-7,7a-dihydro-pyrrolo[1,2-c]oxazole-5-carboxylic acid ethyl ester 在 水 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 25.0h， 生成 (4S,5R)-4-羟基-5-(羟基甲基)-L-脯氨酸
  参考文献：
  名称：

  An efficient, stereoselective synthesis of (−)-bulgecinine from (S)-aspartic acid

  摘要：

  A stereoselective synthesis of (2S,4S,5R)4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)(2)](2) catalyzed stereospecific transformation (de > 98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de > 88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00215-2
• 作为产物：
  描述：

  (5S,7aS)-1,6-dioxo-3,3-bis(trifluoromethyl)-tetrahydro-pyrrolo<1,2-c>oxazole-5-carboxylic acid ethyl ester 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 以79%的产率得到(7aS)-6-hydroxy-1-oxo-3,3-bis(trifluoromethyl)-7,7a-dihydro-pyrrolo[1,2-c]oxazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  An efficient, stereoselective synthesis of (−)-bulgecinine from (S)-aspartic acid

  摘要：

  A stereoselective synthesis of (2S,4S,5R)4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)(2)](2) catalyzed stereospecific transformation (de > 98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de > 88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00215-2

文献信息

• An efficient, stereoselective synthesis of (−)-bulgecinine from (S)-aspartic acid
  作者：Susanna Fehn、Klaus Burger

  DOI：10.1016/s0957-4166(97)00215-2

  日期：1997.6

  A stereoselective synthesis of (2S,4S,5R)4-hydroxy-5-hydroxymethylproline 1 starting from (S)-aspartic acid 2 is described. The key step of the synthesis is the [Rh(OAc)(2)](2) catalyzed stereospecific transformation (de > 98%) of the hexafluoroacetone protected diazoketone 5 into the 4-oxoproline derivative 7. The keto function of 7 was reduced with high diastereoselectivity (de > 88%) to give the 4-cis-hydroxyproline derivative 8. After deprotection (-)-bulgecinine 1 was obtained from 9 on reduction of the ester moiety with LiBHEt3. (C) 1997 Elsevier Science Ltd.