(2R,4R,6R)-4-(carboethoxymethyl)-2-phenyl-6-[(tert-butyl-dimethyl-sil)oxy-ethyl]-1,3-dioxane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R,4R,6R)-4-(carboethoxymethyl)-2-phenyl-6-[(tert-butyl-dimethyl-sil)oxy-ethyl]-1,3-dioxane
• 英文别名: (2R,4R,6R)-4-(carboethoxymethyl)-2-phenyl-6-[(tert-butyl-dimethyl-siloxy)-ethyl]-1,3-dioxane；ethyl 2-[(2R,4R,6R)-6-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2-phenyl-1,3-dioxan-4-yl]acetate
• 化学式: C₂₂H₃₆O₅Si
• 分子量: 408.61
• InChiKey: CKVJRMIEYPKJSY-SFHLNBCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 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 、 三苯基膦 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 四氧化锇 、 正丁基锂 、 甲酸 、 Hydroquinone 1,4-phthalazinediyl diether 、 potassium tert-butylate 、 三乙胺 、 三苯基膦 、 potassium hexacyanoferrate(III) 、 苯酚 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 5.5h， 生成 (2R,4R,6R)-4-(carboethoxymethyl)-2-phenyl-6-[(tert-butyl-dimethyl-sil)oxy-ethyl]-1,3-dioxane
  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

• Asymmetric Iterative Hydration of Polyene Strategy to Cryptocaryols A and B
  作者：George O’Doherty、Thomas Hunter、Yanping Wang、Jiamin Zheng

  DOI：10.1055/s-0035-1561607

  日期：——

  development of two iterative asymmetric hydration approaches to the synthesis of all syn- and syn/anti/syn-1,3,5,7-tetraol motifs is described. These pseudo-symmetric products are synthetic precursors for 1,3-hexol products. The utility of the route to the all syn-1,3,5,7-tetraol diastereoisomer was demonstrated with its use in the synthesis of cryptocaryols A and B, as well as, stereoisomers. The development

  摘要 两种迭代不对称水合的发展接近所有的合成顺式-和顺式/反/顺式-1,3,5,7四醇基序进行说明。这些伪对称产物是1，3-己醇产物的合成前体。证明了该路线对所有syn -1,3,5,7-四醇非对映异构体的实用性，并证明其可用于合成隐甲酚A和B，以及立体异构体。 两种迭代不对称水合的发展接近所有的合成顺式-和顺式/反/顺式-1,3,5,7四醇基序进行说明。这些伪对称产物是1，3-己醇产物的合成前体。证明了该路线对所有syn -1,3,5,7-四醇非对映异构体的实用性，并证明其可用于合成隐甲酚A和B，以及立体异构体。
• 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%).