methyl (4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate | 872831-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 872831-60-2
• 化学式: C₈H₁₃IO₄
• 分子量: 300.093
• InChiKey: UKEYEVKPFUXTCI-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  methyl (4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以95%的产率得到(4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093
• 作为产物：
  描述：

  (4S,5R)-methyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以83%的产率得到methyl (4S,5S)-5-(iodomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093