(E)-(4S,5S,6R)-Methyl 4-acetoxy-7-hydroxy-6-methoxy-5-methylhept-2-enoate | 147059-82-3

• 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: (E)-(4S,5S,6R)-Methyl 4-acetoxy-7-hydroxy-6-methoxy-5-methylhept-2-enoate
• 英文别名: methyl (E,4S,5S,6R)-4-acetyloxy-7-hydroxy-6-methoxy-5-methylhept-2-enoate
• CAS: 147059-82-3
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: GMVSIANNADAMLF-ZUJJTTJYSA-N

物化性质

• 沸点：
  360.2±42.0 °C(predicted)
• 密度：
  1.120±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (E)-(4S,5S,6R)-Methyl 4-acetoxy-7-hydroxy-6-methoxy-5-methylhept-2-enoate 生成 (3R,4R,5R)-2,3-Diacetoxy-5-methoxy-4-methylpyranose 、 (3R,4R,5R)-2,3-Diacetoxy-5-methoxy-4-methylpyranose
  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：

  (E)-(4S,5S,6R)-Methyl 4-acetoxy-7-(benzyloxy)-6-methoxy-5-methylhept-2-enoate 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (E)-(4S,5S,6R)-Methyl 4-acetoxy-7-hydroxy-6-methoxy-5-methylhept-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