(2R,3R,4R,E)-8-oxooct-6-ene-2,3,4-tri-O-acetate | 1439364-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,E)-8-oxooct-6-ene-2,3,4-tri-O-acetate
• 英文别名: [(E,2R,3R,4R)-3,4-diacetyloxy-8-oxooct-6-en-2-yl] acetate
• CAS: 1439364-95-0
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: IXJPRDUUGGRSAB-DKWKPRLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,E)-8-oxooct-6-ene-2,3,4-tri-O-acetate 在 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2R,3R,4R,8R,E)-8-(acryloyloxy)undeca-6,10-diene-2,3,4-tri-O-acetate
  参考文献：
  名称：

  Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

  摘要：

  Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an alpha,alpha'-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee > 99%). After the asymmetric synthesis of the triol fragment of the molecule, the delta-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.

  DOI：

  10.1055/s-0032-1316865
• 作为产物：
  描述：

  (4R,5R,6R)-4-allyl-2,2,6-trimethyl-1,3-dioxan-5-ol 在 盐酸 、 4-二甲氨基吡啶 、 Hoveyda-Grubbs catalyst second generation 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 65.0h， 生成 (2R,3R,4R,E)-8-oxooct-6-ene-2,3,4-tri-O-acetate
  参考文献：
  名称：

  Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology

  摘要：

  Synargentolide A was synthesized in 11 steps starting from the commercially available 2,2-dimethyl-1,3-dioxan-5-one, employing the SAMP/RAMP-methodology via an alpha,alpha'-bis-alkylation to generate the first two stereogenic centers with virtually complete asymmetric induction (de, ee > 99%). After the asymmetric synthesis of the triol fragment of the molecule, the delta-lactone moiety was constructed using an asymmetric allylation, esterification, and ring-closing metathesis sequence.

  DOI：

  10.1055/s-0032-1316865