(3aR,6R,6aR)-N-[(4-methoxyphenyl)methyl]-2,2,6-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-amine | 1301240-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3aR,6R,6aR)-N-[(4-methoxyphenyl)methyl]-2,2,6-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-amine
• CAS: 1301240-39-0
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: QJWULJDZVDHOHE-GCBUYMIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,6R,6aR)-N-[(4-methoxyphenyl)methyl]-2,2,6-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-amine 在 吡啶 、 palladium on carbon 、 氢气 、 甲基磺酰氯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 71.0h， 生成 (3aS,4S,6S,6aR)-4-(4-methoxyphenyl)-2,2,6-trimethyl-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
  参考文献：
  名称：

  Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-epi-(+)-Codonopsinine

  摘要：

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.

  DOI：

  10.1021/jo200176u
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 吡啶 、 palladium on carbon 、 氢气 、 三乙胺 、 sodium iodide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 43.0h， 生成 (3aR,6R,6aR)-N-[(4-methoxyphenyl)methyl]-2,2,6-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-amine
  参考文献：
  名称：

  Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-epi-(+)-Codonopsinine

  摘要：

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.

  DOI：

  10.1021/jo200176u

文献信息

• Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-<i>epi</i>-(+)-Codonopsinine
  作者：Alexis Kotland、Fabien Accadbled、Koen Robeyns、Jean-Bernard Behr

  DOI：10.1021/jo200176u

  日期：2011.5.20

  The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against alpha-fucosidase.