(1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]butyl (2R)-2-(benzyloxy)-5-hexenoate | 1353566-64-9

• 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: (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]butyl (2R)-2-(benzyloxy)-5-hexenoate
• 英文别名: [(1R)-1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]butyl] (2R)-2-phenylmethoxyhex-5-enoate
• CAS: 1353566-64-9
• 化学式: C₂₄H₃₄O₅
• 分子量: 402.531
• InChiKey: LJXWWTFLORXWMV-CBPXPLCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]butyl (2R)-2-(benzyloxy)-5-hexenoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以88%的产率得到(3aR,4R,7R,10Z,11aS)-2,2-dimethyl-7-phenylmethoxy-4-propyl-3a,4,7,8,9,11a-hexahydro-[1,3]dioxolo[4,5-c]oxecin-6-one
  参考文献：
  名称：

  Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides

  摘要：

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.

  DOI：

  10.1021/jo202199g
• 作为产物：
  描述：

  反式-2-已烯-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 L-(+)-酒石酸二异丙酯 、 potassium carbonate 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 25.83h， 生成 (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]butyl (2R)-2-(benzyloxy)-5-hexenoate
  参考文献：
  名称：

  Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides

  摘要：

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.

  DOI：

  10.1021/jo202199g

文献信息

• Titanium(IV)-Promoted Regioselective Nucleophilic Ring-Opening Reaction of Chiral Epoxyallyl Alcohols with Acids as a Tool for Ready Access to Chiral 1,2,3-Triol Monoesters: Application to Stereoselective Total Synthesis of Macrolides
  作者：Palakodety Radha Krishna、D. Venkata Ramana

  DOI：10.1021/jo202199g

  日期：2012.1.6

  Titanium(IV)-promoted regioselective ring-opening reaction of chiral epoxy-allyl alcohols (Sharpless conditions as the key strategic step) is developed as a tool for ready access to chiral 5,6-dihydroxyoct-7-en-4-yl alkoxylates. Later, the synthetic utility of products thereof was demonstrated through the RCM based stereoselective synthesis of various natural products.