(3S,4R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-3-phenylmethoxyoxolan-2-one | 369375-67-7

• 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,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-3-phenylmethoxyoxolan-2-one
• CAS: 369375-67-7
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: XUEALIRRLVDDJF-DGAVXFQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-3-phenylmethoxyoxolan-2-one 在 吡啶 、 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 cerium(III) chloride 、 偶氮二异丁腈 、 三氟化硼乙醚 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 (4S)-2,2-dimethyl-4-[(2S,4S,5S)-5-pentyl-4-phenylmethoxyoxolan-2-yl]-1,3-dioxolane
  参考文献：
  名称：

  Asymmetric synthesis of the new marine epoxy lipid, (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol

  摘要：

  An efficient and stereocontrolled process is described for the preparation of (6S, 7S, 9S, 10S)-6,9-epoxynonadee-18-ene-7.10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by stereoselective hydrogenation of the hemiketal derivative elaborated through nucleophilic addition of Grignard reagent in the presence of CeCl3 to the highly functionalized lactone derived from L-galactono-1,4-lactone,4-lactone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00244-0
• 作为产物：
  描述：

  半乳糖酸內酯 在 对甲苯磺酸 、 silver(l) oxide 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 生成 (3S,4R,5S)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-3-phenylmethoxyoxolan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of the new marine epoxy lipid, (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol

  摘要：

  An efficient and stereocontrolled process is described for the preparation of (6S, 7S, 9S, 10S)-6,9-epoxynonadee-18-ene-7.10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by stereoselective hydrogenation of the hemiketal derivative elaborated through nucleophilic addition of Grignard reagent in the presence of CeCl3 to the highly functionalized lactone derived from L-galactono-1,4-lactone,4-lactone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00244-0

文献信息

• Asymmetric synthesis of the new marine epoxy lipid, (6S,7S,9S,10S)-6,9-epoxynonadec-18-ene-7,10-diol
  作者：Hidemi Yoda、Kazuhide Maruyama、Kunihiko Takabe

  DOI：10.1016/s0957-4166(01)00244-0

  日期：2001.6

  An efficient and stereocontrolled process is described for the preparation of (6S, 7S, 9S, 10S)-6,9-epoxynonadee-18-ene-7.10-diol, a marine epoxy lipid isolated from the brown alga, Notheia anomala. The key 2,3,5-trisubstituted tetrahydrofuran ring was constructed by stereoselective hydrogenation of the hemiketal derivative elaborated through nucleophilic addition of Grignard reagent in the presence of CeCl3 to the highly functionalized lactone derived from L-galactono-1,4-lactone,4-lactone. (C) 2001 Elsevier Science Ltd. All rights reserved.