(R)-3-hydroxy-4-((4S,6S)-6-((S)-2-hydroxybut-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)butyl pivalate | 1290537-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-hydroxy-4-((4S,6S)-6-((S)-2-hydroxybut-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)butyl pivalate
• 英文别名: [(3R)-3-hydroxy-4-[(4S,6S)-6-[(2S)-2-hydroxybut-3-enyl]-2,2-dimethyl-1,3-dioxan-4-yl]butyl] 2,2-dimethylpropanoate
• CAS: 1290537-68-6
• 化学式: C₁₉H₃₄O₆
• 分子量: 358.475
• InChiKey: AOCHXYRRIKMADE-WCVJEAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-3-hydroxy-4-((4S,6S)-6-((S)-2-hydroxybut-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)butyl pivalate 、 tert-butyl (4R,8S,E)-4,8-bis(tert-butyldimethylsilyloxy)undeca-6,10-dienylcarbamate 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以67%的产率得到(R)-4-((4S,6S)-6-((2S,3E,6S,7E,10R)-13-((tert-butoxycarbonyl)amino)-6,10-bis((tert-butyldimethylsilyl)oxy)-2-hydroxytrideca-3,7-dien-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)-3-hydroxybutyl pivalate
  参考文献：
  名称：

  C(21)−C(40) of Tetrafibricin via Metal Catalysis: Beyond Stoichiometric Chiral Reagents, Auxiliaries, and Premetalated Nucleophiles

  摘要：

  The C(21)-C(40) fragment of fibrinogen receptor inhibitor tetrafibricin was prepared in 12 steps from propane diol (longest linear sequence). In this approach, 6 C-C bonds are formed via asymmetric iridium catalyzed transfer hydrogenative carbonyl allylation and 2 C=C bonds are formed via Grubbs olefin cross-metathesis.

  DOI：

  10.1021/ol200735r
• 作为产物：
  描述：

  (R)-3-((tert-butyldiphenylsilyl)oxy)-4-((4R,6R)-6-((S)-2-((tert-butyldiphenylsilyl)oxy)-4-((2-nitrophenyl)selanyl)butyl)-2,2-dimethyl-1,3-dioxan-4-yl)butyl pivalate 在 四丁基氟化铵 、 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 (R)-3-hydroxy-4-((4S,6S)-6-((S)-2-hydroxybut-3-en-1-yl)-2,2-dimethyl-1,3-dioxan-4-yl)butyl pivalate
  参考文献：
  名称：

  C(21)−C(40) of Tetrafibricin via Metal Catalysis: Beyond Stoichiometric Chiral Reagents, Auxiliaries, and Premetalated Nucleophiles

  摘要：

  The C(21)-C(40) fragment of fibrinogen receptor inhibitor tetrafibricin was prepared in 12 steps from propane diol (longest linear sequence). In this approach, 6 C-C bonds are formed via asymmetric iridium catalyzed transfer hydrogenative carbonyl allylation and 2 C=C bonds are formed via Grubbs olefin cross-metathesis.

  DOI：

  10.1021/ol200735r

文献信息

• C(21)−C(40) of Tetrafibricin <i>via</i> Metal Catalysis: Beyond Stoichiometric Chiral Reagents, Auxiliaries, and Premetalated Nucleophiles
  作者：Esa T. T. Kumpulainen、Byungsoo Kang、Michael J. Krische

  DOI：10.1021/ol200735r

  日期：2011.5.6

  The C(21)-C(40) fragment of fibrinogen receptor inhibitor tetrafibricin was prepared in 12 steps from propane diol (longest linear sequence). In this approach, 6 C-C bonds are formed via asymmetric iridium catalyzed transfer hydrogenative carbonyl allylation and 2 C=C bonds are formed via Grubbs olefin cross-metathesis.