5-(hydroxymethyl)-1-(((4S,5R)-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-4,5-dihydrofuran-2-yl)methyl)-1H-pyrrole-2-carbaldehyde | 1395104-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(hydroxymethyl)-1-(((4S,5R)-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-4,5-dihydrofuran-2-yl)methyl)-1H-pyrrole-2-carbaldehyde
• 英文别名: 5-(hydroxymethyl)-1-[[(2R,3S)-3-tri(propan-2-yl)silyloxy-2-[tri(propan-2-yl)silyloxymethyl]-2,3-dihydrofuran-5-yl]methyl]pyrrole-2-carbaldehyde
• CAS: 1395104-87-6
• 化学式: C₃₀H₅₅NO₅Si₂
• 分子量: 565.941
• InChiKey: IDKGJJYYIDJVNI-XZWHSSHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.83
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(hydroxymethyl)-1-(((4S,5R)-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-4,5-dihydrofuran-2-yl)methyl)-1H-pyrrole-2-carbaldehyde 在 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以47%的产率得到(2R,5S)-5-(((triisopropylsilyl)oxy)methyl)-1',4'-dihydro-5H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
  参考文献：
  名称：

  Stereoselective Synthesis of Acortatarins A and B

  摘要：

  Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.

  DOI：

  10.1021/ol3019456
• 作为产物：
  描述：

  1H-吡咯-2,5-二甲醛 在 sodium tetrahydroborate 、 四丁基碘化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 13.83h， 生成 5-(hydroxymethyl)-1-(((4S,5R)-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-4,5-dihydrofuran-2-yl)methyl)-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Stereoselective Synthesis of Acortatarins A and B

  摘要：

  Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.

  DOI：

  10.1021/ol3019456

文献信息

• Stereoselective Synthesis of Acortatarins A and B
  作者：Jacqueline M. Wurst、Alyssa L. Verano、Derek S. Tan

  DOI：10.1021/ol3019456

  日期：2012.9.7

  Acortatarins A and B have been synthesized via stereoselective spirocyclizations of glycals. Mercury-mediated spirocyclization of a pyrrole monoalcohol side chain leads to acortatarin A. Glycal epoxidation and reductive spirocyclization of a pyrrole dialdehyde side chain leads to acortatarin B. Acid equilibration and crystallographic analysis indicate that acortatarin B is a contrathermodynamic spiroketal with distinct ring conformations compared to acortatarin A.