(3S)-4-tert-butoxycarbonylamino-3-((2S,4R)-N-tert-butoxycarbonyl-4-hydroxypyrrolidin-2-yl)butyric acid | 204912-64-1

• 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: (3S)-4-tert-butoxycarbonylamino-3-((2S,4R)-N-tert-butoxycarbonyl-4-hydroxypyrrolidin-2-yl)butyric acid
• 英文别名: (3S)-3-[(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 204912-64-1
• 化学式: C₁₈H₃₂N₂O₇
• 分子量: 388.461
• InChiKey: FUVMAMJNRYYRBX-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S)-4-tert-butoxycarbonylamino-3-((2S,4R)-N-tert-butoxycarbonyl-4-hydroxypyrrolidin-2-yl)butyric acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到(2S,4R)-N-tert-butoxycarbonyl-((3S)-N-tert-butoxycarbonylpyrrolidin-3-yl)-4-hydroxypyrrolidine
  参考文献：
  名称：

  An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step

  摘要：

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00007-6
• 作为产物：
  描述：

  (2S,4R)-2-[(S)-1-(tert-Butoxycarbonylamino-methyl)-2-methoxycarbonyl-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 反应 20.0h， 生成 (3S)-4-tert-butoxycarbonylamino-3-((2S,4R)-N-tert-butoxycarbonyl-4-hydroxypyrrolidin-2-yl)butyric acid
  参考文献：
  名称：

  An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step

  摘要：

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00007-6

文献信息

• An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step
  作者：Norikazu Ohtake、Yasuyuki Imai、Ryosuke Ushijima

  DOI：10.1016/s0040-4020(98)00007-6

  日期：1998.3

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.