(4R,5R)-3-{5-[2-(tert-butyl-dimethyl-siloxy)-ethyl]-2-oxo-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester | 337508-91-5

• 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: (4R,5R)-3-{5-[2-(tert-butyl-dimethyl-siloxy)-ethyl]-2-oxo-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester
• 英文别名: ethyl (E)-3-[(4R,5R)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2-oxo-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 337508-91-5
• 化学式: C₁₆H₂₈O₆Si
• 分子量: 344.48
• InChiKey: CUZRXBSESLXVET-RYYBZQDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-3-{5-[2-(tert-butyl-dimethyl-siloxy)-ethyl]-2-oxo-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester 在 三苯基膦 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 甲酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到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：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 甲基磺酰胺 、 potassium carbonate 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 正丁基锂 、 Hydroquinone 1,4-phthalazinediyl diether 、 三苯基膦 、 potassium hexacyanoferrate(III) 、 苯酚 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 1.5h， 生成 (4R,5R)-3-{5-[2-(tert-butyl-dimethyl-siloxy)-ethyl]-2-oxo-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester
  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

文献信息

• 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%).