ethyl (4S,5R)-5-[(1S,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(4-methoxyphenoxy)propyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate | 871110-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (4S,5R)-5-[(1S,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(4-methoxyphenoxy)propyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 871110-57-5
• 化学式: C₂₄H₄₀O₇Si
• 分子量: 468.663
• InChiKey: RBNNGWGFQNMHLF-ZXNZYJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (4S,5R)-5-[(1S,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(4-methoxyphenoxy)propyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以61%的产率得到(4S,5R)-5-[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Anamarine and Its Analogues

  摘要：

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

  DOI：

  10.1021/jo051681p
• 作为产物：
  描述：

  ethyl (E)-3-[(4S,5S)-5-methyl-2-oxo-1,3-dioxolan-4-yl]prop-2-enoate 在 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 甲基磺酰胺 、 camphor-10-sulfonic acid 、 potassium carbonate 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 58.0h， 生成 ethyl (4S,5R)-5-[(1S,2S)-2-[tert-butyl(dimethyl)silyl]oxy-1-(4-methoxyphenoxy)propyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  De Novo Asymmetric Synthesis of Anamarine and Its Analogues

  摘要：

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.

  DOI：

  10.1021/jo051681p

文献信息

• De Novo Asymmetric Synthesis of Anamarine and Its Analogues
  作者：Dong Gao、George A. O'Doherty

  DOI：10.1021/jo051681p

  日期：2005.11.1

  The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.