((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)methyl 2,4,6-trimethylbenzenesulfonate | 1325653-53-9

• 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,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)methyl 2,4,6-trimethylbenzenesulfonate
• 英文别名: [(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-1,3-benzodioxin-5-yl)propyl]oxan-2-yl]methyl 2,4,6-trimethylbenzenesulfonate
• CAS: 1325653-53-9
• 化学式: C₂₈H₃₆O₇S
• 分子量: 516.656
• InChiKey: WCBORLUBSGQCBL-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)methyl 2,4,6-trimethylbenzenesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以91.3%的产率得到5-(3-((2S,6S)-6-(iodomethyl)tetrahydro-2H-pyran-2-yl)propyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
  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：

  (2R,3S)-3-(dimethyl(phenyl)silyl)-2-((trimethylsilyl)oxy)pent-4-en-1-yl 2,4,6-trimethylbenzenesulfonate 在 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 ((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)methyl 2,4,6-trimethylbenzenesulfonate
  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

文献信息

• Total Synthesis of (+)-SCH 351448
  作者：Kaicheng Zhu、James S. Panek

  DOI：10.1021/ol201863b

  日期：2011.9.2

  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.