7-{(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester | 154633-82-6

• 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: 7-{(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
• 英文别名: methyl 7-[(1S,2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-5-oxocyclopentyl]heptanoate
• CAS: 154633-82-6
• 化学式: C₃₃H₆₄O₅Si₂
• 分子量: 597.039
• InChiKey: JHNSMPGOXWDDJL-MZMIFIKDSA-N

物化性质

• 沸点：
  577.4±50.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.62
• 重原子数：
  40
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-{(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester 在 吡啶 、 氢氟酸 、 L-Selectride 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 7-[(1S,2R,3R,5R)-3,5-Dihydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-heptanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of isoprostanes via the two-component coupling process

  摘要：

  A short total synthesis of isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. The F-1-isoprostanes were easily obtained by stereoselective reduction of the C-9 keto group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00898-5
• 作为产物：
  描述：

  (1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene 、 (R)-(+)-3-(叔丁基二甲基硅氧基)-5-氧代-1-环戊烯基-1-己酸甲酯 生成 11,15-O-bis(tert-butyldimethylsilyl)PGE₁ methyl ester 、 7-{(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
  参考文献：
  名称：

  Total synthesis of isoprostanes via the two-component coupling process

  摘要：

  A short total synthesis of isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. The F-1-isoprostanes were easily obtained by stereoselective reduction of the C-9 keto group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00898-5

文献信息

• Total synthesis of E1 and E2 isoprostanes by diastereoselective protonation
  作者：Ana R. Rodrı́guez、Bernd W. Spur

  DOI：10.1016/s0040-4039(02)02252-9

  日期：2002.12

  A short total synthesis of the E-type isoprostanes has been achieved using a two-component coupling process combined with a diastereoselective protonation under reagent control. Mild cleavage of the silyl protective groups with cat. BiBr3 or HF/Py followed by enzymatic hydrolysis of the methyl ester afforded the free E-type isoprostanes.

  在试剂控制下，使用二组分偶联工艺与非对映选择性质子化相结合，已实现了E型异前列腺素的短暂全合成。与猫的甲硅烷基保护基团的轻度裂解。BiBr 3或HF / Py，然后进行甲酯的酶促水解，得到游离的E型异前列腺素。
• A highly efficient approach to prostaglandins via radical addition of α side-chains to methylenecyclopentanones. Total synthesis of natural PGE1, limaprost and new prostaglandin derivatives.
  作者：Naoya Ono、Yukio Yoshida、Kousuke Tani、Sentaro Okamoto、Fumie Sato

  DOI：10.1016/0040-4039(93)85062-2

  日期：1993.10

  Reaction of methylenecyclopentanones2 with alkyl iodides via radical 1,4-addition pathway proceeds in good yields, thus providing an easy method for synthesis of not only known prostaglandins such as PGE1 and Limafrost but also new prostaglandin derivatives.

  亚甲基环戊酮2通过自由基1,4-加成途径与烷基碘的反应以良好的收率进行，因此不仅为已知的前列腺素（如PGE 1和利马弗罗斯特）而且为新的前列腺素衍生物的合成提供了简便的方法。