2-[(2R,6S)-6-((2S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-7-{(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-trimethylsilanyloxy-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester | 858346-77-7

• 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: 2-[(2R,6S)-6-((2S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-7-{(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-trimethylsilanyloxy-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester
• 英文别名: 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-trimethylsilyloxyheptyl]oxan-2-yl]-2-methylpropanoate
• CAS: 858346-77-7
• 化学式: C₆₁H₈₆O₉Si₂
• 分子量: 1019.52
• InChiKey: BRWVVWOXQPMKIW-YMCOOTEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.91
• 重原子数：
  72
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[(2R,6S)-6-((2S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-7-{(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-trimethylsilanyloxy-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester 在 吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88%的产率得到2-[(2R,6S)-6-((2R,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-5-methyl-7-{(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester
  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：

  2-{(2R,6S)-6-[(4R,5S)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-4-hydroxy-5-methyl-2-oxo-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 咪唑 、 4-二甲氨基吡啶 、 potassium phosphate 、 溶剂黄146 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 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 34.0h， 生成 2-[(2R,6S)-6-((2S,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-7-{(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-trimethylsilanyloxy-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester
  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.