(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester | 223246-02-4

• 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,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(1S)-1-hydroxyprop-2-enyl]-1-[(4-methoxyphenyl)methyl]-4-methyl-5-oxopyrrolidine-2-carboxylate
• CAS: 223246-02-4
• 化学式: C₂₄H₃₇NO₆Si
• 分子量: 463.646
• InChiKey: SPRAZNZATLSYBH-VUYBDXIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester 在 水 、 三氟乙酸 作用下， 反应 4.0h， 生成 (2R,3S,4R)-3-Hydroxy-2-((S)-1-hydroxy-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The structural requirements for inhibition of proteasome function by the lactacystin-derived ?-lactone and synthetic analogs

  摘要：

  The synthesis of analogs of the lactacystin-derived beta-lactone (2) in which the substituents at C(5), C(7) and C(9) were systematically varied has led to a well defined structure-activity correlation for the highly selective inhibition of the mammalian 20 S proteasome. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01142-9
• 作为产物：
  描述：

  乙烯基溴化镁 、 methyl (2S,3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-2-formyl-1-[(4-methoxyphenyl)methyl]-4-methyl-5-oxopyrrolidine-2-carboxylate 在 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以93%的产率得到(2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-hydroxy-allyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The structural requirements for inhibition of proteasome function by the lactacystin-derived ?-lactone and synthetic analogs

  摘要：

  The synthesis of analogs of the lactacystin-derived beta-lactone (2) in which the substituents at C(5), C(7) and C(9) were systematically varied has led to a well defined structure-activity correlation for the highly selective inhibition of the mammalian 20 S proteasome. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01142-9