(4R,5R,6R)-4-allyl-2,2,6-trimethyl-1,3-dioxan-5-ol | 1439364-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R,6R)-4-allyl-2,2,6-trimethyl-1,3-dioxan-5-ol
• 英文别名: (4R,5R,6R)-2,2,4-trimethyl-6-prop-2-enyl-1,3-dioxan-5-ol
• CAS: 1439364-93-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: MFWPAMPSJBAJDA-IWSPIJDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 (2R,3R,4R)-hept-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
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 草酸 作用下， 以 乙醇 、 正己烷 、 水 为溶剂， 反应 15.0h， 生成 (4R,5R,6R)-4-allyl-2,2,6-trimethyl-1,3-dioxan-5-ol
  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

文献信息

• Asymmetric Synthesis of Synargentolide A and Its 3-Epimer Using the RAMP-Hydrazone Methodology
  作者：Dieter Enders、Linus Reichenbach

  DOI：10.1055/s-0032-1316865

  日期：——

  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.