5-benzyloxy-6-[1,3]dithian-2-yl-3-hydroxy-6-methyl-heptanoic acid methyl ester | 335119-28-3

• 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: 5-benzyloxy-6-[1,3]dithian-2-yl-3-hydroxy-6-methyl-heptanoic acid methyl ester
• 英文别名: methyl (3S,5S)-6-(1,3-dithian-2-yl)-3-hydroxy-6-methyl-5-phenylmethoxyheptanoate
• CAS: 335119-28-3
• 化学式: C₂₀H₃₀O₄S₂
• 分子量: 398.588
• InChiKey: UZQLAFRHRYWRIP-IRXDYDNUSA-N

物化性质

• 熔点：
  45-48 °C
• 沸点：
  547.3±50.0 °C(predicted)
• 密度：
  1.174±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-benzyloxy-6-[1,3]dithian-2-yl-3-hydroxy-6-methyl-heptanoic acid methyl ester 在 tetramethylammonium triacetoxyborohydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 溶剂黄146 、 乙腈 为溶剂， 反应 98.0h， 生成 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：

  1,3-丙二硫醇 、 (4-benzyloxy-6-hydroxy-5,5-dimethyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester 在 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 反应 0.5h， 以95%的产率得到5-benzyloxy-6-[1,3]dithian-2-yl-3-hydroxy-6-methyl-heptanoic acid methyl 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

文献信息

• Asymmetric Synthesis of the Northern Half C1−C16 of the Bryostatins
  作者：A. Vakalopoulos、T. F. J. Lampe、H. M. R. Hoffmann

  DOI：10.1021/ol015551o

  日期：2001.3.1

  [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.