2-[(2R,6S)-6-((2R,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester | 858346-78-8

• 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: 2-[(2R,6S)-6-((2R,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester
• 英文别名: benzyl 2-[(2R,6S)-6-[(2R,4R,5S)-2-[tert-butyl(dimethyl)silyl]oxy-7-[(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]-4-hydroxy-5-methylheptyl]oxan-2-yl]-2-methylpropanoate
• CAS: 858346-78-8
• 化学式: C₄₈H₇₄O₉Si
• 分子量: 823.196
• InChiKey: DMINDAQNWBLHAW-NJQSYVEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.89
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-[(2R,6S)-6-((2R,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester 在 2,2-diphenyl-benzo[1,3]dioxin-4-one derivative 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到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}-2,4-dihydroxy-5-methyl-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 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 potassium phosphate 、 氟化氢吡啶 、 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 43.5h， 生成 2-[(2R,6S)-6-((2R,4R,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-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