(2S,4R,5S)-2-(benzyloxy)-7-((2S,6S)-6-(3-(3-(benzyloxy)-2-((2-(trimethylsilyl)ethoxy)carbonyl)phenyl)propyl)tetrahydro-2H-pyran-2-yl)-1-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-5-methylheptan-4-yl 2-(3-((2S,6S)-6-((3S,4R,6S)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)-6-hydroxybenzoate | 1325653-90-4

• 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: (2S,4R,5S)-2-(benzyloxy)-7-((2S,6S)-6-(3-(3-(benzyloxy)-2-((2-(trimethylsilyl)ethoxy)carbonyl)phenyl)propyl)tetrahydro-2H-pyran-2-yl)-1-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-5-methylheptan-4-yl 2-(3-((2S,6S)-6-((3S,4R,6S)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)-6-hydroxybenzoate
• CAS: 1325653-90-4
• 化学式: C₁₁₀H₁₅₄O₁₇Si₂
• 分子量: 1804.59
• InChiKey: KSTPZJBKPNQJPZ-KBXAJTJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.58
• 重原子数：
  129.0
• 可旋转键数：
  49.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  199.27
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (2S,4R,5S)-2-(benzyloxy)-7-((2S,6S)-6-(3-(3-(benzyloxy)-2-((2-(trimethylsilyl)ethoxy)carbonyl)phenyl)propyl)tetrahydro-2H-pyran-2-yl)-1-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-5-methylheptan-4-yl 2-(3-((2S,6S)-6-((3S,4R,6S)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)-6-hydroxybenzoate 、 溴甲苯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以96%的产率得到(2S,4R,5S)-2-(benzyloxy)-7-((2S,6S)-6-(3-(3-(benzyloxy)-2-((2-(trimethylsilyl)ethoxy)carbonyl)phenyl)propyl)tetrahydro-2H-pyran-2-yl)-1-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-5-methylheptan-4-yl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)benzoate
  参考文献：
  名称：

  Total Synthesis of (+)-SCH 351448

  摘要：

  A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C-2-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide.

  DOI：

  10.1021/ol201863b
• 作为产物：
  描述：

  benzyl 2-((2R,6S)-6-((2S,4R,5S)-2-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-7-((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)-5-methylheptyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate 、 2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6R)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-hydroxy-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)benzoate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以63%的产率得到(2S,4R,5S)-2-(benzyloxy)-7-((2S,6S)-6-(3-(3-(benzyloxy)-2-((2-(trimethylsilyl)ethoxy)carbonyl)phenyl)propyl)tetrahydro-2H-pyran-2-yl)-1-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-5-methylheptan-4-yl 2-(3-((2S,6S)-6-((3S,4R,6S)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)-6-hydroxybenzoate
  参考文献：
  名称：

  Total Synthesis of (+)-SCH 351448

  摘要：

  A convergent synthesis of (+)-SCH 351448 (1), a monosodium salt of a C-2-symmetric macrodiolide, is described. Our approach is based on a [4 + 2] annulation with a chiral allyl silane (anti-5c) to assemble the pyran subunits. Homodimerization was carried out in a stepwise fashion; initial esterification at C29' followed by macrocyclization at C29 afforded the desired macrodiolide.

  DOI：

  10.1021/ol201863b