(3S,4R)-5-((4-methoxybenzyl)oxy)-4-methylpentane-1,3-diol | 1453868-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R)-5-((4-methoxybenzyl)oxy)-4-methylpentane-1,3-diol
• 英文别名: (3S,4R)-5-[(4-methoxyphenyl)methoxy]-4-methylpentane-1,3-diol
• CAS: 1453868-10-4
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: BJETWZFFHNRXQQ-RISCZKNCSA-N

物化性质

• 沸点：
  418.1±40.0 °C(predicted)
• 密度：
  1.101±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-5-((4-methoxybenzyl)oxy)-4-methylpentane-1,3-diol 在 吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 aluminum (III) chloride 、 copper(l) iodide 、 硼烷四氢呋喃络合物 、 L-(+)-酒石酸二乙酯 、 L-(+)-酒石酸二异丙酯 、 三丁基膦 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 、 (R)-2-甲基-CBS-恶唑硼烷 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 358.0h， 生成 C₃₄H₆₀O₇Si
  参考文献：
  名称：

  Total Synthesis and Structural Revision of Sekothrixide

  摘要：

  The first total synthesis of 14-membered macrolide sekothrbdde and the originally proposed structure are reported. Seven contiguous asymmetric centers in the side chain were constructed using ring-openings of several kinds of epoxide. Assembly of the left segment and right segment was performed on the basis of the RCM reaction to generate 14-membered lactones having an E-trisubstituted olefin. These synthetic results led to a revision of C4, C6, and C8 stereochemistry in the structure of natural sekothrixide.

  DOI：

  10.1021/ol5006856
• 作为产物：
  描述：

  (R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate 在 咪唑 、 sodium perborate monohydrate 、 四丁基氟化铵 、 异丙基氯化镁 、 三乙胺 、 copper(l) chloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 28.5h， 生成 (3S,4R)-5-((4-methoxybenzyl)oxy)-4-methylpentane-1,3-diol
  参考文献：
  名称：

  Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations

  摘要：

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.

  DOI：

  10.1021/jo401293a

文献信息

• Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations
  作者：Casey Medina、Kyle P. Carter、Michael Miller、Timothy B. Clark、Gregory W. O’Neil

  DOI：10.1021/jo401293a

  日期：2013.9.20

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.
• Total Synthesis and Structural Revision of Sekothrixide
  作者：Naoki Terayama、Eiko Yasui、Megumi Mizukami、Masaaki Miyashita、Shinji Nagumo

  DOI：10.1021/ol5006856

  日期：2014.6.6

  The first total synthesis of 14-membered macrolide sekothrbdde and the originally proposed structure are reported. Seven contiguous asymmetric centers in the side chain were constructed using ring-openings of several kinds of epoxide. Assembly of the left segment and right segment was performed on the basis of the RCM reaction to generate 14-membered lactones having an E-trisubstituted olefin. These synthetic results led to a revision of C4, C6, and C8 stereochemistry in the structure of natural sekothrixide.