(Z)-5-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]pent-3-enoic acid | 390746-28-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-5-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]pent-3-enoic acid
• CAS: 390746-28-8
• 化学式: C₃₆H₇₂O₅Si₃
• 分子量: 669.221
• InChiKey: QOYJYFXPIZXIBU-VXMRHNRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.35
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-5-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]pent-3-enoic acid 在 甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到前列腺素
  参考文献：
  名称：

  iPF2α-III metabolism. First total synthesis of 2,3-dinor iPF2α-III, a primary β-oxidation metabolite

  摘要：

  The total synthesis of a primary iPF(2 alpha)-III metabolite, namely dinor iPF(2 alpha)-III 8, is described. The successful synthesis was finally accomplished by generating the carboxylic acid group at the end of the synthesis so as to avoid formation of an alpha,beta -unsaturated carboxylic acid, which is prone to undergo side reactions (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01794-4
• 作为产物：
  描述：

  methyl (E,4S,6R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[(4S)-2-sulfanylidene-1,3-dioxolan-4-yl]hex-2-enoate 在 sodium chlorite 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 偶氮二异丁腈 、 (S)-BINAL-H 、 米帕明 、 potassium tert-butylate 、 三正丁基氢锡 、 二甲基氯化铝 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 30.0h， 生成 (Z)-5-[(1S,2R,3R,5S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]cyclopentyl]pent-3-enoic acid
  参考文献：
  名称：

  iPF2α-III metabolism. First total synthesis of 2,3-dinor iPF2α-III, a primary β-oxidation metabolite

  摘要：

  The total synthesis of a primary iPF(2 alpha)-III metabolite, namely dinor iPF(2 alpha)-III 8, is described. The successful synthesis was finally accomplished by generating the carboxylic acid group at the end of the synthesis so as to avoid formation of an alpha,beta -unsaturated carboxylic acid, which is prone to undergo side reactions (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01794-4

文献信息

• iPF2α-III metabolism. First total synthesis of 2,3-dinor iPF2α-III, a primary β-oxidation metabolite
  作者：Seongjin Kim、Young-Ju Jung、John A Lawson、Garret A FitzGerald、Joshua Rokach

  DOI：10.1016/s0040-4039(01)01794-4

  日期：2001.11

  The total synthesis of a primary iPF(2 alpha)-III metabolite, namely dinor iPF(2 alpha)-III 8, is described. The successful synthesis was finally accomplished by generating the carboxylic acid group at the end of the synthesis so as to avoid formation of an alpha,beta -unsaturated carboxylic acid, which is prone to undergo side reactions (C) 2001 Elsevier Science Ltd. All rights reserved.