(-)-(2R,3S,4S,5R)-3-hydroxy-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde | 1395104-91-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(2R,3S,4S,5R)-3-hydroxy-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde
• 英文别名: (3R,3'S,4'S,5'R)-3'-hydroxy-4'-tri(propan-2-yl)silyloxy-5'-[tri(propan-2-yl)silyloxymethyl]spiro[1,4-dihydropyrrolo[2,1-c][1,4]oxazine-3,2'-oxolane]-6-carbaldehyde
• CAS: 1395104-91-2
• 化学式: C₃₀H₅₅NO₆Si₂
• 分子量: 581.941
• InChiKey: OALSQAIBJRRESI-GKIKGMKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3S,4S,5R)-3-hydroxy-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-1',4,4',5-tetrahydro-3H-spiro[furan-2,3'-pyrrolo[2,1-c][1,4]oxazine]-6'-carbaldehyde 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以91%的产率得到acortatarin B
  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 二甲基二环氧乙烷 、 四丁基碘化铵 、 tetrabutylammonium borohydride 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 16.83h， 生成 (-)-(2R,3S,4S,5R)-3-hydroxy-4-(triisopropylsilyloxy)-5-((triisopropylsilyloxy)methyl)-1',4,4',5-tetrahydro-3H-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

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.