(2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate | 143446-41-7

• 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: (2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate
• 英文别名: methyl (E,2R,3R)-2-acetyloxy-3-[dimethyl(phenyl)silyl]hex-4-enoate
• CAS: 143446-41-7
• 化学式: C₁₇H₂₄O₄Si
• 分子量: 320.461
• InChiKey: WJZQXWIVECNEKB-ZLAMNEIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate 在 双(乙腈)氯化钯(II) 、 三氟甲磺酸三甲基硅酯 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 (E)-(4R,5S,6R)-Methyl 4-acetoxy-6-methoxy-5-methyl-7-hydroxy-hept-2-enoate
  参考文献：
  名称：

  Sequential diastereoselective addition and palladium(II)-catalyzed allylic acetate transposition of syn- and anti-.alpha.-acetoxy-.beta.-silyl-(E)-hex-4-enoates with achiral acetals. Asymmetric synthesis of differentiated syn and anti 1,3-diol synthons

  摘要：

  syn- and anti-methyl alpha-acetoxy-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates, (2R,3R)-8a and (2S,3R)-8b, undergo highly diastereo- and enantioselective addition reactions with aldehydes and acetals 11 catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) generating alpha-acetoxy-beta,-gamma-unsaturated esters (allylic acetates) 12. A subsequent allylic acetate transposition promoted by dichloropalladium bisacetonitrile complex, PdCl2(MeCN)2 afforded the differentiated 1,3-diol synthons 13.

  DOI：

  10.1021/jo00057a008
• 作为产物：
  描述：

  (3S)-(E)-1-(Dimethylphenylsilyl)-1-buten-3-yl hydroxyacetate 在 4-二甲氨基吡啶 吡啶 、 正丁基锂 、 三甲基氯硅烷 、 氯化亚砜 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (2R,3R)-(E)-Methyl 2-acetoxy-3-(dimethylphenylsilyl)-hex-4-enoate
  参考文献：
  名称：

  Sequential diastereoselective addition and palladium(II)-catalyzed allylic acetate transposition of syn- and anti-.alpha.-acetoxy-.beta.-silyl-(E)-hex-4-enoates with achiral acetals. Asymmetric synthesis of differentiated syn and anti 1,3-diol synthons

  摘要：

  syn- and anti-methyl alpha-acetoxy-beta-(dimethylphenylsilyl)-(E)-hex-4-enoates, (2R,3R)-8a and (2S,3R)-8b, undergo highly diastereo- and enantioselective addition reactions with aldehydes and acetals 11 catalyzed by the action of trimethylsilyl trifluoromethanesulfonate (TMSOTf) generating alpha-acetoxy-beta,-gamma-unsaturated esters (allylic acetates) 12. A subsequent allylic acetate transposition promoted by dichloropalladium bisacetonitrile complex, PdCl2(MeCN)2 afforded the differentiated 1,3-diol synthons 13.

  DOI：

  10.1021/jo00057a008

文献信息

• Diastereoselective additions of chiral (E)-crotylsilanes to in situ generated oxonium ions: a direct asymmetric synthesis of functionalized homoallylic ethers
  作者：James S. Panek、Michael Yang、Feng Xu

  DOI：10.1021/jo00047a046

  日期：1992.10