(1S,2R,3S,4S)-4-(benzyloxy)-1-phenyloct-7-ene-1,2,3-triol | 944353-01-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1S,2R,3S,4S)-4-(benzyloxy)-1-phenyloct-7-ene-1,2,3-triol
• 英文别名: (1S,2R,3S,4S)-1-phenyl-4-phenylmethoxyoct-7-ene-1,2,3-triol
• CAS: 944353-01-9
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: UCZSBVGHLIKGMT-UWHLTILDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4S)-4-(benzyloxy)-1-phenyloct-7-ene-1,2,3-triol 在 碳酸氢钠 、 臭氧 、 二甲基硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R,2S)-1-[(2S,3S)-6-hydroxy-3-phenylmethoxyoxan-2-yl]-2-phenylethane-1,2-diol
  参考文献：
  名称：

  Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin

  摘要：

  [GRAPHICS]Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.

  DOI：

  10.1021/jo0702342
• 作为产物：
  描述：

  ((S)-1-((4S,5R)-5-((S)-1-(benzyloxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)-tert-butyldimethylsilane 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以84%的产率得到(1S,2R,3S,4S)-4-(benzyloxy)-1-phenyloct-7-ene-1,2,3-triol
  参考文献：
  名称：

  Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-epi-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin

  摘要：

  [GRAPHICS]Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.

  DOI：

  10.1021/jo0702342

文献信息

• Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-<i>epi</i>-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo0702342

  日期：2008.1.1

  [GRAPHICS]Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.