(S)-4-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2-methyl-butyraldehyde | 404890-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (S)-4-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2-methyl-butyraldehyde
• 英文别名: (2S)-2-methyl-4-[(2S,6R)-6-prop-2-enyloxan-2-yl]butanal
• CAS: 404890-46-6
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: RSWVNWGQFMEGNL-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2-methyl-butyraldehyde 在 camphor-10-sulfonic acid 、 三乙胺 、 diethylboron trifluoromethanesulfonate 作用下， 以 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 6.0h， 生成 2-((2R,6S)-6-{(4S,6R)-6-[(S)-3-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-1-methyl-propyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-tetrahydro-pyran-2-yl)-2-methyl-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448

  摘要：

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

  DOI：

  10.1021/ol016938u
• 作为产物：
  描述：

  Thiocarbonic acid O-[(1R,2S)-1-((2S,6R)-6-allyl-tetrahydro-pyran-2-ylmethyl)-3-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2-methyl-3-oxo-propyl] ester O-phenyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 8.0h， 生成 (S)-4-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2-methyl-butyraldehyde
  参考文献：
  名称：

  Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448

  摘要：

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.

  DOI：

  10.1021/ol016938u

文献信息

• Synthesis of the C1−C21 (C1‘-C21‘) Fragment of the Dimeric Polyketide Natural Product SCH 351448
  作者：Ashoke Bhattacharjee、Omid Soltani、Jef K. De Brabander

  DOI：10.1021/ol016938u

  日期：2002.2.1

  A convergent, stereoselective assembly of the C1-C21 (Cl'-C21') fragment of SCH 351448, a 28-membered bis-lactose natural product, has been developed. A highly efficient approach to this fragment assembles 75% of the carbon skeleton and all the stereochemical elements present in the natural product. In addition, an interesting boron ligand effect on the diastereoselectivity of a key aldol reaction with methyl ketone-derived enolborinates is reported.