(2R,3R,4R,5S)-5-Methoxy-2,4-dimethyl-hexane-1,3-diol | 155813-70-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3R,4R,5S)-5-Methoxy-2,4-dimethyl-hexane-1,3-diol
• 英文别名: (2R,3R,4R,5S)-5-methoxy-2,4-dimethylhexane-1,3-diol
• CAS: 155813-70-0
• 化学式: C₉H₂₀O₃
• 分子量: 176.256
• InChiKey: QEMJBAWXITYQIC-RYPBNFRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 (2R,3R,4R,5S)-5-Methoxy-2,4-dimethyl-hexane-1,3-diol 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以90%的产率得到(2S,3S)-3-<(2R,4R,5R)-5-Methyl-2-phenyl-1,3-dioxan-4-yl>-2-methoxybutane
  参考文献：
  名称：

  Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin

  摘要：

  The tandem iodoetherification reaction and stereoselective reduction of acyclic radicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans. Such a tetrahydrofuran intermediate is regioselectively cleaved using Me(2)BBr to reveal the acyclic array 2 which represents the C-17-C-22 subunit of ionomycin. In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radical are imbedded in a cycle (''cycle effect''). A mechanistic rationale is discussed.

  DOI：

  10.1021/jo00084a040
• 作为产物：
  描述：

  diethyl (2S,3R)-2-methylmalate 在 偶氮二异丁腈 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基溴化硼 、 三乙基硼 、 dimethyl sulfide borane 、 四丁基氟化铵 、 碘 、 三正丁基氢锡 、 sodium hydride 、 碳酸氢钠 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 114.33h， 生成 (2R,3R,4R,5S)-5-Methoxy-2,4-dimethyl-hexane-1,3-diol
  参考文献：
  名称：

  Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin

  摘要：

  The tandem iodoetherification reaction and stereoselective reduction of acyclic radicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans. Such a tetrahydrofuran intermediate is regioselectively cleaved using Me(2)BBr to reveal the acyclic array 2 which represents the C-17-C-22 subunit of ionomycin. In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radical are imbedded in a cycle (''cycle effect''). A mechanistic rationale is discussed.

  DOI：

  10.1021/jo00084a040

文献信息

• Stereoselective Hydrogen Transfer Reactions Involving Acyclic Radicals. Tandem Substituted Tetrahydrofuran Formation and Stereoselective Reduction: Synthesis of the C17-C22 Subunit of Ionomycin
  作者：Y. Guindon、C. Yoakim、V. Gorys、W. W. Ogilvie、D. Delorme、J. Renaud、G. Robinson、J.-F. Lavallee、A. Slassi

  DOI：10.1021/jo00084a040

  日期：1994.3

  The tandem iodoetherification reaction and stereoselective reduction of acyclic radicals has been used in the stereocontrolled synthesis of substituted tetrahydrofurans. Such a tetrahydrofuran intermediate is regioselectively cleaved using Me(2)BBr to reveal the acyclic array 2 which represents the C-17-C-22 subunit of ionomycin. In experiments that provide for a better understanding of hydrogen transfer reactions involving acyclic radicals, a significant improvement in the stereoselectivity is observed when the two substituents at the stereogenic center alpha to the radical are imbedded in a cycle (''cycle effect''). A mechanistic rationale is discussed.