[(2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazinyl]-2-[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethanone | 281681-89-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazinyl]-2-[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethanone
• 英文别名: [(2R,3R,3aR,4S,5R,6S)-5-benzoyloxy-2-[2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxyacetyl]-3-[dimethyl(phenyl)silyl]-6-[(1R)-2,2-diphenylcyclopentyl]oxy-2,3,3a,4,5,6-hexahydro-[1,2]oxazolo[2,3-b]oxazin-4-yl] benzoate
• CAS: 281681-89-8
• 化学式: C₅₅H₆₅NO₉Si₂
• 分子量: 940.293
• InChiKey: RHQOBDWHPDAOFF-QFDKUFSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.46
• 重原子数：
  67
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazinyl]-2-[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethanone 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (αR,2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)-α-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazine-2-methanol 、 (αS,2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)-α-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazine-2-methanol
  参考文献：
  名称：

  Synthesis of (+)-Casuarine

  摘要：

  The first synthesis of (+)-casuarine ((+)-6), a pentahydroxy pyrrolizidine alkaloid of the alexine/ australine subclass, is described. The key step is a tandem [4 + 2]/[3 + 2] nitroalkene cycloaddition involving nitrobenzoate 13, chiral vinyl ether 16c, and vinyl silane 10, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis requires only four additional steps to deliver the final product in 20% overall yield.

  DOI：

  10.1021/jo991680v
• 作为产物：
  描述：

  苯甲酰氟 在 四丁基氟化铵 、 四氯化锡 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 20.0h， 生成 [(2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazinyl]-2-[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]ethanone
  参考文献：
  名称：

  Synthesis of (+)-Casuarine

  摘要：

  The first synthesis of (+)-casuarine ((+)-6), a pentahydroxy pyrrolizidine alkaloid of the alexine/ australine subclass, is described. The key step is a tandem [4 + 2]/[3 + 2] nitroalkene cycloaddition involving nitrobenzoate 13, chiral vinyl ether 16c, and vinyl silane 10, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis requires only four additional steps to deliver the final product in 20% overall yield.

  DOI：

  10.1021/jo991680v

文献信息

• Synthesis of (+)-Casuarine
  作者：Scott E. Denmark、Alexander R. Hurd

  DOI：10.1021/jo991680v

  日期：2000.5.1

  The first synthesis of (+)-casuarine ((+)-6), a pentahydroxy pyrrolizidine alkaloid of the alexine/ australine subclass, is described. The key step is a tandem [4 + 2]/[3 + 2] nitroalkene cycloaddition involving nitrobenzoate 13, chiral vinyl ether 16c, and vinyl silane 10, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis requires only four additional steps to deliver the final product in 20% overall yield.