2-(p-tolylsulfonyl)ethyl (2E,4R,5R,7R)-4,5,7-trihydroxy-2-octenoate | 91273-90-4

• 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-(p-tolylsulfonyl)ethyl (2E,4R,5R,7R)-4,5,7-trihydroxy-2-octenoate
• CAS: 91273-90-4
• 化学式: C₁₇H₂₄O₇S
• 分子量: 372.439
• InChiKey: XRVWDJPFSKOSMM-KBMXLJTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  121.13
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(p-tolylsulfonyl)ethyl (2E,4R,5R,7R)-4,5,7-trihydroxy-2-octenoate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 25.0 ℃ 、1.96 MPa 条件下， 反应 104.0h， 生成 2-(p-tolylsulfonyl)ethyl (10E,4S,5S,7R,13S)-13-t-butyldimethylsiloxy-4,5-isopropylidenedioxy-7-methyl-9-oxo-8-oxa-10-tetradecenoate
  参考文献：
  名称：

  Formal total synthesis of grahamimycin A1

  摘要：

  (S)-t-Butyldimethylsiloxy-2-hexenoic acid and its (R)-isomer were prepared from (S)- and (R)-3-hydroxybutanoic acid esters, respectively. Condensation of the both isomers with 2-(ptoluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-4,5-dimethylmethylenedioxyoctanoate, synthesized from methyl 4,6-dideoxy -alpha-D-xylo-hexopyranoside, gave the corresponding esters which were converted into precursors of seco acids of grahamimycin A1 with S or R configuration at the C-6 position (grahamimycin A1 numbering). The (6S)- and (6R)-isomers were respectively subjected to macrolactonization by the use of diethyl azodicarboxylate-triphenylphosphine system or Yamaguchi procedure to afford 11, 12-dihydroxy-grahamimycin A1 whose oxidation to grahamimycin A1 has already been reported.

  DOI：

  10.1016/s0040-4039(00)79484-6
• 作为产物：
  描述：

  methyl 4,6-dideoxy-α-D-glucopyranoside 在 Dowex-50W (H+) 、 水 作用下， 以 苯 为溶剂， 反应 30.0h， 生成 2-(p-tolylsulfonyl)ethyl (2E,4R,5R,7R)-4,5,7-trihydroxy-2-octenoate
  参考文献：
  名称：

  Formal total synthesis of grahamimycin A1

  摘要：

  (S)-t-Butyldimethylsiloxy-2-hexenoic acid and its (R)-isomer were prepared from (S)- and (R)-3-hydroxybutanoic acid esters, respectively. Condensation of the both isomers with 2-(ptoluenesulfonyl)ethyl (4S,5S,7R)-7-hydroxy-4,5-dimethylmethylenedioxyoctanoate, synthesized from methyl 4,6-dideoxy -alpha-D-xylo-hexopyranoside, gave the corresponding esters which were converted into precursors of seco acids of grahamimycin A1 with S or R configuration at the C-6 position (grahamimycin A1 numbering). The (6S)- and (6R)-isomers were respectively subjected to macrolactonization by the use of diethyl azodicarboxylate-triphenylphosphine system or Yamaguchi procedure to afford 11, 12-dihydroxy-grahamimycin A1 whose oxidation to grahamimycin A1 has already been reported.

  DOI：

  10.1016/s0040-4039(00)79484-6