tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate | 129980-28-5

• 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: tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate
• 英文别名: tert-butyl (2S)-2-(aminomethyl)-3-[1-[[(2S)-1-[(2-methylpropan-2-yl)oxy]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1-oxopropan-2-yl]carbamoyl]cyclopentyl]propanoate
• CAS: 129980-28-5
• 化学式: C₃₁H₅₀N₂O₆
• 分子量: 546.748
• InChiKey: YLYXQSNTHHEXGA-UPVQGACJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate 在 5%-palladium/activated carbon 、 氢气 、 1-羟基苯并三唑 、 苯甲醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 10.0~35.0 ℃ 、413.7 kPa 条件下， 反应 13.0h， 生成 山帕曲拉
  参考文献：
  名称：

  The Chemical Development and Scale-Up of Sampatrilat¹

  摘要：

  The discovery and scale-up of two routes to sampatrilat are described. The first Chemical R and D route used a side product from another development project to accelerate drug supply and expedite the early development programme. The second, more efficient Chemical R and D route had the potential for commercialisation and used an environmentally friendly variant of the Baylis-Hillman reaction, and an asymmetric Michael addition as key steps. Full preparative details for the aminomethacrylate 4, a potentially useful chiral synthon, are given for the first time, along with full experimental details of the asymmetric Michael addition to make the chiral glutarate 5. Finally, a striking polymorph case history is described.

  DOI：

  10.1021/op020091f
• 作为产物：
  描述：

  tert-butyl 2-hydroxymethylacrylate 在 吡啶 、 氯化亚砜 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， -30.0~50.0 ℃ 、413.7 kPa 条件下， 生成 tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate
  参考文献：
  名称：

  The Chemical Development and Scale-Up of Sampatrilat¹

  摘要：

  The discovery and scale-up of two routes to sampatrilat are described. The first Chemical R and D route used a side product from another development project to accelerate drug supply and expedite the early development programme. The second, more efficient Chemical R and D route had the potential for commercialisation and used an environmentally friendly variant of the Baylis-Hillman reaction, and an asymmetric Michael addition as key steps. Full preparative details for the aminomethacrylate 4, a potentially useful chiral synthon, are given for the first time, along with full experimental details of the asymmetric Michael addition to make the chiral glutarate 5. Finally, a striking polymorph case history is described.

  DOI：

  10.1021/op020091f

文献信息

• Asymmetric synthesis of β-amino acid derivatives by Michael addition to chiral 2-aminomethylacrylates
  作者：Ian T. Barnish、Martin Corless、Peter J. Dunn、David Ellis、Paul.W. Finn、J.David Hardstone、Keith James

  DOI：10.1016/s0040-4039(00)91786-6

  日期：1993.2

  The addition of lithium enolates to chiral aminomethylacrylates 7 and 8 proceeded with excellent diastereodifferentiation (up to 98% de) and provided an expeditious synthesis of homochiral β-aminomethylglutarates 9 and 10, on a scale of up to 500g. The acrylates 7 and 8, and their antipodes, should be useful synthons for the synthesis of β-amino acid derivatives.

  向手性氨基甲基丙烯酸酯7和8中添加烯醇锂进行出色的非对映体分化（高达98％de），并以最大500g的规模快速合成了手性β-氨基甲基戊二酸酯9和10。丙烯酸酯7和8及其对映体应该是合成β-氨基酸衍生物的有用的合成子。
• US5208236A
  申请人：——

  公开号：US5208236A

  公开（公告）日：1993-05-04