benzyl 2-[(2R,6S)-6-[(2S,4R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-methyl-7-[(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]-4-(2,2,2-trifluoroacetyl)oxyheptyl]oxan-2-yl]-2-methylpropanoate | 858346-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: benzyl 2-[(2R,6S)-6-[(2S,4R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-methyl-7-[(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]-4-(2,2,2-trifluoroacetyl)oxyheptyl]oxan-2-yl]-2-methylpropanoate
• CAS: 858346-80-2
• 化学式: C₆₀H₇₇F₃O₁₀Si
• 分子量: 1043.35
• InChiKey: XCYVTGUTMRDOJS-MDZSIBPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.17
• 重原子数：
  74
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-[(2R,6S)-6-((2R,4R,5S)-7-{(2S,6S)-6-[3-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-2-methoxymethoxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester 、 benzyl 2-[(2R,6S)-6-[(2S,4R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-methyl-7-[(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]-4-(2,2,2-trifluoroacetyl)oxyheptyl]oxan-2-yl]-2-methylpropanoate 以 二氯甲烷 为溶剂， 反应 1.0h， 以27%的产率得到[(2S,4R,5S)-7-[(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]-2-(methoxymethoxy)-5-methyl-1-[(2S,6R)-6-(2-methyl-1-oxo-1-phenylmethoxypropan-2-yl)oxan-2-yl]heptan-4-yl] 2-[3-[(2S,6S)-6-[(3S,4R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-3-methyl-7-[(2S,6R)-6-(2-methyl-1-oxo-1-phenylmethoxypropan-2-yl)oxan-2-yl]-4-(2,2,2-trifluoroacetyl)oxyheptyl]oxan-2-yl]propyl]-6-hydroxybenzoate
  参考文献：
  名称：

  A Concise Synthesis of (+)-SCH 351448

  摘要：

  yWe describe a highly convergent synthetic approach to the natural product (+)-SCH 351448 (1)-a hexane-soluble heptacoordinate monosodium salt of a C-2-symmetrical macrocyclic dilactone. Our approach implements a photochemical acylation as the key step to combine two nearly identical but orthogonal C1-C29 fragments, followed by a base-induced intramolecular acylation and deprotection to yield the natural product.

  DOI：

  10.1021/ol0510769
• 作为产物：
  描述：

  trifluoromethanesulfonic acid 4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 吡啶 、 potassium phosphate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 benzyl 2-[(2R,6S)-6-[(2S,4R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-5-methyl-7-[(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]-4-(2,2,2-trifluoroacetyl)oxyheptyl]oxan-2-yl]-2-methylpropanoate
  参考文献：
  名称：

  A Concise Synthesis of (+)-SCH 351448

  摘要：

  yWe describe a highly convergent synthetic approach to the natural product (+)-SCH 351448 (1)-a hexane-soluble heptacoordinate monosodium salt of a C-2-symmetrical macrocyclic dilactone. Our approach implements a photochemical acylation as the key step to combine two nearly identical but orthogonal C1-C29 fragments, followed by a base-induced intramolecular acylation and deprotection to yield the natural product.

  DOI：

  10.1021/ol0510769

文献信息

• A Concise Synthesis of (+)-SCH 351448
  作者：Omid Soltani、Jef K. De Brabander

  DOI：10.1021/ol0510769

  日期：2005.6.1

  yWe describe a highly convergent synthetic approach to the natural product (+)-SCH 351448 (1)-a hexane-soluble heptacoordinate monosodium salt of a C-2-symmetrical macrocyclic dilactone. Our approach implements a photochemical acylation as the key step to combine two nearly identical but orthogonal C1-C29 fragments, followed by a base-induced intramolecular acylation and deprotection to yield the natural product.