methyl 4-[(4S,5S)-5-decyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]butanoate | 188576-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: methyl 4-[(4S,5S)-5-decyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]butanoate
• CAS: 188576-26-3
• 化学式: C₁₇H₃₂O₆S
• 分子量: 364.503
• InChiKey: LQNZDOTUKXALHV-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-[(4S,5S)-5-decyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]butanoate 在 吡啶 、 lithium hydroxide 、 硫酸 作用下， 反应 36.0h， 生成 6-acetoxy-5-hexadecanolide
  参考文献：
  名称：

  Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone

  摘要：

  Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00011-6
• 作为产物：
  描述：

  4-((4S,5S)-5-Decyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-butyric acid methyl ester 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.0h， 以91%的产率得到methyl 4-[(4S,5S)-5-decyl-2,2-dioxo-1,3,2-dioxathiolan-4-yl]butanoate
  参考文献：
  名称：

  Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone

  摘要：

  Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00011-6

文献信息

• Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone
  作者：Braj B. Lohray、S. Venkateswarlu

  DOI：10.1016/s0957-4166(97)00011-6

  日期：1997.2

  Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (C) 1997 Elsevier Science Ltd.