(S,E)-6-((4S,5R)-5-((R)-1-hydroxyoctyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-enoic acid | 1586033-57-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S,E)-6-((4S,5R)-5-((R)-1-hydroxyoctyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-enoic acid
• CAS: 1586033-57-9
• 化学式: C₂₁H₃₈O₇
• 分子量: 402.529
• InChiKey: CBTCXXUBQZNXFB-RAAAAISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  28.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S,E)-6-((4S,5R)-5-((R)-1-hydroxyoctyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-enoic acid 在 4-二甲氨基吡啶 、 2-甲基-6-硝基苯甲酸酐 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以68%的产率得到(3aR,4R,9S,11aS,E)-4-heptyl-9-(methoxymethoxy)-2,2-dimethyl-7,8,9,11a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]oxecin-6(4H)-one
  参考文献：
  名称：

  Asymmetric synthesis of naturally occurring nonenolide xyolide through cross metathesis and macrolactonization reaction

  摘要：

  Asymmetric total synthesis of xyolide, a small ring macrolide is presented in this article. The synthesis is achieved through an 'E' selective cross metathesis (CM) reaction between two appropriate fragments followed by lactonization by Shiina method. One of the fragments containing 7S,8S,9R stereocenters of xyolide is accessed from n-nonanal by adopting an organocatalytic asymmetric alpha-aminooxylation, Z-selective Ando olefination, and substrate directed dihydroxylation reaction. The other fragments containing 4S stereocenter was prepared by ME-DKR (metal enzyme combined dynamic kinetic resolution) method. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.072
• 作为产物：
  描述：

  tert-butyl-((R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)octyloxy)diphenylsilane 在 sodium chlorite 、 sodium dihydrogenphosphate 、 Hoveyda-Grubbs catalyst second generation 、 2-甲基-2-丁烯 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 34.0h， 生成 (S,E)-6-((4S,5R)-5-((R)-1-hydroxyoctyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-enoic acid
  参考文献：
  名称：

  Asymmetric synthesis of naturally occurring nonenolide xyolide through cross metathesis and macrolactonization reaction

  摘要：

  Asymmetric total synthesis of xyolide, a small ring macrolide is presented in this article. The synthesis is achieved through an 'E' selective cross metathesis (CM) reaction between two appropriate fragments followed by lactonization by Shiina method. One of the fragments containing 7S,8S,9R stereocenters of xyolide is accessed from n-nonanal by adopting an organocatalytic asymmetric alpha-aminooxylation, Z-selective Ando olefination, and substrate directed dihydroxylation reaction. The other fragments containing 4S stereocenter was prepared by ME-DKR (metal enzyme combined dynamic kinetic resolution) method. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.072