(2E,4E,7R)-8-[tert-butyl(dimethyl)silyl]oxy-2,7-dimethylocta-2,4-dien-1-ol | 208193-37-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2E,4E,7R)-8-[tert-butyl(dimethyl)silyl]oxy-2,7-dimethylocta-2,4-dien-1-ol
• CAS: 208193-37-7
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: FSSIHIBUGYGPHB-DSSDBPQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E,7R)-8-[tert-butyl(dimethyl)silyl]oxy-2,7-dimethylocta-2,4-dien-1-ol 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2,7-Dimethyl-8-hydroxy-4(E),6(E)-octadien-1-yl-β-D-glucopyranoside pentaacetate
  参考文献：
  名称：

  Synthesis of a Glycosidic Precursor of Isomeric Marmelo Oxides, Volatile Components of Quince Fruit, Cydonia oblonga

  摘要：

  Synthesis of (R)-8-hydroxy-2,7-dimethyl-(4E,6E)-octadienyl beta-D-glucopyranoside (1), a glycosidic precursor of marmelo oxides, the volatile components of quince fruit, Cydonia oblonga Mill., was achieved starting from (S)-3-hydroxy-2-methylpropanoate (5). The conjugated diene moiety was constructed in one step by a Horner reaction, and the final glycosidation was executed via the chloroimidate method.

  DOI：

  10.1021/np970480g
• 作为产物：
  描述：

  methyl (E)-4-(diethoxyphosphoryl)-2-methylbut-2-enoate 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (2E,4E,7R)-8-[tert-butyl(dimethyl)silyl]oxy-2,7-dimethylocta-2,4-dien-1-ol
  参考文献：
  名称：

  Synthesis of a Glycosidic Precursor of Isomeric Marmelo Oxides, Volatile Components of Quince Fruit, Cydonia oblonga

  摘要：

  Synthesis of (R)-8-hydroxy-2,7-dimethyl-(4E,6E)-octadienyl beta-D-glucopyranoside (1), a glycosidic precursor of marmelo oxides, the volatile components of quince fruit, Cydonia oblonga Mill., was achieved starting from (S)-3-hydroxy-2-methylpropanoate (5). The conjugated diene moiety was constructed in one step by a Horner reaction, and the final glycosidation was executed via the chloroimidate method.

  DOI：

  10.1021/np970480g

文献信息

• Synthesis of the Glycosidic Precursor of Isomeric Marmelo Lactones, Volatile Components of the Quince Fruit,<i>Cydonia oblonga</i>
  作者：Hiroki SHIMIZU、Takeshi KITAHARA

  DOI：10.1271/bbb.66.743

  日期：2002.1

  The glucosidic precursor of marmelo lactones was synthesized by employing a common intermediate which had been used for the synthesis of the glucosidic precursor of marmelo oxides. The synthesis was performed by modifying the former procedure. Monochloroacetyl was adopted to protect both the glucose and aglycon hydroxyl groups for selective transesterification in the presence of the glycosyl ester

  marmelo内酯的糖苷前体是通过使用一种常见的中间体合成的，该中间体已用于合成marmelo氧化物的糖苷前体。通过修改前一步骤进行合成。在糖基酯存在下，采用一氯乙酰基保护葡萄糖和糖苷配基羟基以进行选择性酯交换。用1-α-溴过一氯乙酰基葡萄糖对糖苷配基的糖基化作用和最终的选择性醇解产生了目标糖苷。
• Synthesis of a Glycosidic Precursor of Isomeric Marmelo Oxides, Volatile Components of Quince Fruit, <i>Cydonia oblonga</i>
  作者：Takeshi Kitahara、Hiroki Shimizu

  DOI：10.1021/np970480g

  日期：1998.4.1

  Synthesis of (R)-8-hydroxy-2,7-dimethyl-(4E,6E)-octadienyl beta-D-glucopyranoside (1), a glycosidic precursor of marmelo oxides, the volatile components of quince fruit, Cydonia oblonga Mill., was achieved starting from (S)-3-hydroxy-2-methylpropanoate (5). The conjugated diene moiety was constructed in one step by a Horner reaction, and the final glycosidation was executed via the chloroimidate method.