(2R,3S,4S)-4-(2-methoxy-6-methoxycarbonylpyridin-3-yl)-3-(2-methoxy-2-oxoethyl)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid | 1585241-72-0

• 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: (2R,3S,4S)-4-(2-methoxy-6-methoxycarbonylpyridin-3-yl)-3-(2-methoxy-2-oxoethyl)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 1585241-72-0
• 化学式: C₂₄H₂₆N₂O₉
• 分子量: 486.478
• InChiKey: BCARSXMQOWQSNT-SQGPQFPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-4-(2-methoxy-6-methoxycarbonylpyridin-3-yl)-3-(2-methoxy-2-oxoethyl)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid 在 水 、 氢溴酸 、 sodium acetate 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 37.0h， 生成 5-[(3S,4S,5S)-5-羧基-4-(羧甲基)-3-吡咯烷基]-6-氧代-1,6-二氢-2-吡啶羧酸
  参考文献：
  名称：

  Practical Total Syntheses of Acromelic Acids A and B

  摘要：

  Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.

  DOI：

  10.1021/ol500529w
• 作为产物：
  描述：

  2,6-二氯吡啶 在 1,1'-双(二苯基膦)二茂铁 、 氯化亚砜 、 Ni(OAc)2-(H₂O)4-(S,S)-N,N'-dibenzylcyclohexane-1,2-diamine complex 、 palladium 10% on activated carbon 、 氢气 、 叔丁基锂 、 sodium acetate 、 palladium diacetate 、 甲基磺酰氯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正庚烷 、 二氯甲烷 、 甲苯 为溶剂， -78.0~75.0 ℃ 、6.21 MPa 条件下， 反应 76.0h， 生成 (2R,3S,4S)-4-(2-methoxy-6-methoxycarbonylpyridin-3-yl)-3-(2-methoxy-2-oxoethyl)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Practical Total Syntheses of Acromelic Acids A and B

  摘要：

  Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.

  DOI：

  10.1021/ol500529w

文献信息

• Practical Total Syntheses of Acromelic Acids A and B
  作者：Hitoshi Ouchi、Aya Asahina、Tomohiro Asakawa、Makoto Inai、Yoshitaka Hamashima、Toshiyuki Kan

  DOI：10.1021/ol500529w

  日期：2014.4.4

  Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.