ethyl (4R,5R)-7-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-heptenoate | 337508-89-1

• 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: ethyl (4R,5R)-7-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-heptenoate
• 英文别名: ethyl (E,4R,5R)-7-[tert-butyl(dimethyl)silyl]oxy-4,5-dihydroxyhept-2-enoate
• CAS: 337508-89-1
• 化学式: C₁₅H₃₀O₅Si
• 分子量: 318.486
• InChiKey: BIZZWRWZFNZHHY-RYYBZQDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (4R,5R)-7-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-heptenoate 在 三苯基膦 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 甲酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 ethyl (5S)-7-(tert-butyl-dimethyl-siloxy)-5-hydroxy-2-heptenoate
  参考文献：
  名称：

  An Enantioselective Synthesis of Benzylidene-Protected syn-3,5-Dihydroxy Carboxylate Esters via Osmium, Palladium, and Base Catalysis

  摘要：

  [GRAPHICS]The enantioselective syntheses of several protected syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral 1,3-dieneoates, The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form delta -hydroxy-1-enoates, The resulting delta -hydroxy-1-enoates are subsequently converted into benzylidene-protected 3,5-dihydroxy carboxylic esters in one step, The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (25% to 51%) and high enantiomeric excesses (80% to >95%).

  DOI：

  10.1021/ol0156188
• 作为产物：
  描述：

  4-(叔丁基二甲基甲硅烷基)氧代-1-丁醇 在 potassium osmate(VI) dihydrate 、 (DHQD)2PHAL 、 甲基磺酰胺 、 K₃[Fe(CN)6] 、 sodium acetate 、 potassium carbonate 、 三苯基膦 、 pyridinium chlorochromate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 33.5h， 生成 ethyl (4R,5R)-7-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-heptenoate
  参考文献：
  名称：

  Topsentolide B 2的全合成

  摘要：

  基于不对称二羟基化，Roush烯丙基化和闭环易位（RCM）反应，已经实现了托酚类化合物B 2（针对SK-OV-3和SK-MEL-2癌细胞系的选择性细胞毒性脂蛋白）的立体选择性全合成。合成过程分11个步骤完成，总产率为2.1％。

  DOI：

  10.1016/j.tetlet.2011.02.014

文献信息

• Asymmetric total synthesis of (+)-cardiobutanolide via an iterative asymmetric dihydroxylation in PEG
  作者：S. Chandrasekhar、N. Kiranmai

  DOI：10.1016/j.tetlet.2010.05.122

  日期：2010.8

  The stereoselective total synthesis of (+)-cardiobutanolide, a polyhydroxylated natural product, is achieved in high yield through Lu and Guo diene synthesis, Sharpless asymmetric dihydroxylation, and one-pot deprotection–lactonization. The utility of a recyclable reagent system in PEG for asymmetric dihydroxylation is demonstrated.

  通过Lu和Guo二烯合成，Sharpless不对称二羟基化和一锅脱保护-内酯化，可以高收率地实现多羟基化天然产物（+）-心脏丁醇内酯的立体选择性全合成。证明了可回收试剂系统在PEG中用于不对称二羟基化的实用性。
• An Enantioselective Synthesis of Benzylidene-Protected <i>syn</i>-3,5-Dihydroxy Carboxylate Esters via Osmium, Palladium, and Base Catalysis
  作者：Thomas J. Hunter、George A. O'Doherty

  DOI：10.1021/ol0156188

  日期：2001.4.1

  [GRAPHICS]The enantioselective syntheses of several protected syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral 1,3-dieneoates, The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form delta -hydroxy-1-enoates, The resulting delta -hydroxy-1-enoates are subsequently converted into benzylidene-protected 3,5-dihydroxy carboxylic esters in one step, The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (25% to 51%) and high enantiomeric excesses (80% to >95%).
• Total synthesis of topsentolide B2
  作者：Rodney A. Fernandes、Pullaiah Kattanguru

  DOI：10.1016/j.tetlet.2011.02.014

  日期：2011.4

  A stereoselective total synthesis of topsentolide B2, a selective cytotoxic oxylipin against SK-OV-3 and SK-MEL-2 cancer cell lines has been achieved based on asymmetric dihydroxylation, Roush allylation, and ring closing metathesis (RCM) reactions. The synthesis is completed in 11 steps and 2.1% overall yield.

  基于不对称二羟基化，Roush烯丙基化和闭环易位（RCM）反应，已经实现了托酚类化合物B 2（针对SK-OV-3和SK-MEL-2癌细胞系的选择性细胞毒性脂蛋白）的立体选择性全合成。合成过程分11个步骤完成，总产率为2.1％。