(2R*,4S*,6S*)-2-tert-butyl-6-hexyl-4-methyl-1,3-dioxane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R*,4S*,6S*)-2-tert-butyl-6-hexyl-4-methyl-1,3-dioxane
• 英文别名: (2R,4S,6S)-2-tert-butyl-4-hexyl-6-methyl-1,3-dioxane
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: SPYXFUOMODMVRO-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2S,6S)-2-tert-Butyl-6-hexyl-[1,3]dioxan-4-ol 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R*,4S*,6S*)-2-tert-butyl-6-hexyl-4-methyl-1,3-dioxane
  参考文献：
  名称：

  Dialkylzinc Additions to 4-Acetoxy-1,3-dioxanes:  A Highly Stereoselective Route to Protected anti-1,3-Diols

  摘要：

  DOI：

  10.1021/jo971207m

文献信息

• <i>Anti</i>-1,3-diols by Addition of Dialkylzinc Reagents to 4-Acetoxy-1,3-dioxanes
  作者：Noel A. Powell、Scott D. Rychnovsky

  DOI：10.1021/jo982264y

  日期：1999.3.1

  Dialkylzincs couple with 4-acetoxy-6-alkyl-1,3-dioxanes in the presence of trimethylsilyl triflate (TMSOTf) to form trans-4,6-dialkyl-1,3-dioxanes with excellent diastereoselectivities. These dioxanes could be deprotected to yield anti-1,3-diols. A variety of functional groups are tolerated in the dialkylzinc, although silyl and benzyl ethers led to diminished diastereoselectivities. Substituents at the C5-position of the dioxane ring have little effect on the selectivity, while small C2 (acetal) substituents led to slightly reduced diastereoselectivity. These couplings work best with cyclic acetals, which can be difficult to hydrolyze. The 4-(benzyloxy)butanal (BOB) acetal has been developed as a new cyclic acetal protecting group that is compatible with dialkylzinc coupling reactions. BOB protecting groups are easily removed by catalytic hydrogenation followed by mild acid hydrolysis.
• Dialkylzinc Additions to 4-Acetoxy-1,3-dioxanes:  A Highly Stereoselective Route to Protected <i>anti</i>-1,3-Diols
  作者：Scott D. Rychnovsky、Noel A. Powell

  DOI：10.1021/jo971207m

  日期：1997.9.1