(3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one | 286408-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one
• 英文别名: (4S,5R,6S)-6-[(2R)-but-3-en-2-yl]-4-[(4-methoxyphenyl)methoxy]-5-methyloxan-2-one
• CAS: 286408-58-0
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: AJRFMPSDAPSCNG-GQGSAGHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸乙酯 、 (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 以60%的产率得到[(2S,4S,5R,6S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of the C1−C9 Fragment of Callipeltoside-A

  摘要：

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

  DOI：

  10.1021/ol006003y
• 作为产物：
  描述：

  (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol 在 四丙基高钌酸铵 、 双(三甲基硅基)过氧化物 、 四氯化锡 、 1,2-二氨基环己烷 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 (3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one
  参考文献：
  名称：

  Synthesis of the C1−C9 Fragment of Callipeltoside-A

  摘要：

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

  DOI：

  10.1021/ol006003y

文献信息

• The Meinwald reaction of alkyl propionates. Synthesis of the C1–C9 fragment of aurisides
  作者：Marı́a-Yolanda Rı́os、Francisco Velázquez、Horacio F Olivo

  DOI：10.1016/s0040-4020(03)01064-0

  日期：2003.8

  The C1–C9 northern fragment of aurisides 12a was prepared in eight steps and 41% overall yield starting from Grieco's bicyclic lactone (+)-4. The synthesis features a key stereoselective Meinwald reaction of the lithium enolate of alkyl propionate with the functionalized δ-lactone 3.

  从Grieco的双环内酯（+）- 4开始，八步制备C1-C9北方苷12a的片段，总产率为41％。该合成的特征在于丙酸烷基酯的烯醇锂与官能化的δ-内酯3的关键立体选择性Meinwald反应。
• Synthesis of the C1−C9 Fragment of Callipeltoside-A
  作者：Francisco Velázquez、Horacio F. Olivo

  DOI：10.1021/ol006003y

  日期：2000.6.1

  The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.