7-benzyloxy-8-[1,3]dithian-2-yl-5-hydroxy-8-methyl-3-oxo-nonanoic acid tert-butyl ester | 335119-31-8

• 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: 7-benzyloxy-8-[1,3]dithian-2-yl-5-hydroxy-8-methyl-3-oxo-nonanoic acid tert-butyl ester
• CAS: 335119-31-8
• 化学式: C₂₅H₃₈O₅S₂
• 分子量: 482.706
• InChiKey: LOWNSJBCDPBNQG-CTNGQTDRSA-N

物化性质

• 沸点：
  619.7±55.0 °C(predicted)
• 密度：
  1.151±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-8-[1,3]dithian-2-yl-5-hydroxy-8-methyl-3-oxo-nonanoic acid tert-butyl ester 在 tetramethylammonium triacetoxyborohydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 96.0h， 生成 7-benzyloxy-8-[1,3]dithian-2-yl-3,5-dihydroxy-8-methyl-nonanoic acid tert-butyl ester 、 7-benzyloxy-8-[1,3]dithian-2-yl-3,5-dihydroxy-8-methyl-nonanoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o
• 作为产物：
  描述：

  (4-benzyloxy-6-hydroxy-5,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 在 三氟化硼乙醚 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 硝基甲烷 为溶剂， 反应 2.5h， 生成 7-benzyloxy-8-[1,3]dithian-2-yl-5-hydroxy-8-methyl-3-oxo-nonanoic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins

  摘要：

  [GRAPHICS]Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence), Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.

  DOI：

  10.1021/ol015551o