ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate | 871110-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate
• 英文别名: ethyl (2S,3S,4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxy-4-(4-methoxyphenoxy)hexanoate
• CAS: 871110-63-3
• 化学式: C₂₁H₃₆O₇Si
• 分子量: 428.598
• InChiKey: ISWKQXVFDVSZAE-UDTPNQRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate 在 zinc(II) tetrahydroborate 、 ammonium cerium(IV) nitrate 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 43.67h， 生成 ethyl (4S,5R)-5-[(1R,2S)-1,2-dihydroxypropyl]-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
• 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 、 potassium carbonate 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 22.0h， 生成 ethyl (2S,3S,4S,5S)-4-(4-methoxyphenoxy)-5-(tert-butyl-dimethyl-siloxy)-2,3-dihydroxyhexanoate
  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.