(2S,4R)-4-[(1R)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester | 1446911-14-3

• 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: (2S,4R)-4-[(1R)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester
• CAS: 1446911-14-3
• 化学式: C₃₃H₄₁N₃O₈S
• 分子量: 639.77
• InChiKey: WQYWCQVKOINXDN-RUZUFKRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  131.55
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-[(1R)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 3.5h， 生成 (2S,4R)-4-[(1R)-2-methoxy-2-oxo-1-[(phenylmethoxy)amino]ethyl]-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester
  参考文献：
  名称：

  Total synthesis of penmacric acids via an intermolecular radical addition reaction

  摘要：

  The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-L-proline. Furthermore, 1',3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.006
• 作为产物：
  描述：

  Cbz-L-羟脯氨酸 在 三乙基硼 、 硫酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 28.0h， 生成 (2S,4R)-4-[(1R)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester 、 (2S,4R)-4-[(1S)-2-[(3aR,6S,7aS)-tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-oxo-1-(phenylmethoxy)amino]ethyl-1-(phenylmethoxy)carbonyl-2-pyrrolidinecarboxylic acid methyl ester
  参考文献：
  名称：

  Total synthesis of penmacric acids via an intermolecular radical addition reaction

  摘要：

  The total syntheses of penmacric acid and its three stereoisomers were accomplished through the intermolecular radical addition reaction of the 4-pyrrolidyl radical derived from trans-4-hydroxy-L-proline. Furthermore, 1',3-diepi-penmacric acid was synthesized stereoselectively via double stereoinduction in the radical reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.006