ethyl (4R,5R)-6-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-hexenoate | 337508-88-0

• 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)-6-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-hexenoate
• 英文别名: ethyl (E,4R,5R)-6-[tert-butyl(dimethyl)silyl]oxy-4,5-dihydroxyhex-2-enoate
• CAS: 337508-88-0
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: SLUXLDHZKUVNGU-SVKHLYGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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)-6-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-hexenoate 在 吡啶 、 4-二甲氨基吡啶 、 (1S)-(+)-10-camphorsulfonic acid 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.5h， 生成 (4R,5R)-3-[5-(4-methoxy-benzyloxymethyl)-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
• 作为产物：
  描述：

  ethyl 6-((tert-butyldimethylsilyl)oxy)hex-2-ynoate 在 甲基磺酰胺 、 potassium carbonate 四氧化锇 、 Hydroquinone 1,4-phthalazinediyl diether 、 三苯基膦 、 potassium hexacyanoferrate(III) 、 苯酚 作用下， 以 水 、 叔丁醇 为溶剂， 生成 ethyl (4R,5R)-6-(tert-butyl-dimethyl-siloxy)-4,5-dihydroxy-2-hexenoate
  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%).