(2S,3S,4S,5R)-2-(but-3-enyl)-tetrahydro-5-phenylfuran-3,4-diol | 887927-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R)-2-(but-3-enyl)-tetrahydro-5-phenylfuran-3,4-diol
• 英文别名: (2S,3S,4S,5R)-2-but-3-enyl-5-phenyloxolane-3,4-diol
• CAS: 887927-63-1
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: MCZNNJQBJWPMQM-RFQIPJPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R)-2-(but-3-enyl)-tetrahydro-5-phenylfuran-3,4-diol 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 (2R,3R,3aS,7aS)-2-phenyl-3,3a,5,6,7,7a-hexahydro-2H-furo[3,2-b]pyran-3,5-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：

  (4S,5R)-5-((S)-hydroxy(phenyl)methyl)-N,N,2,2-tetramethyl-1,3-dioxolane-4-carboxamide 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三氯化铁 、 L-Selectride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 (2S,3S,4S,5R)-2-(but-3-enyl)-tetrahydro-5-phenylfuran-3,4-diol
  参考文献：
  名称：

  Stereoselective Synthesis of (+)-Goniothalesdiol

  摘要：

  Stereoselective synthesis of antitumor tetrahydrofuran (+)-goniothalesdiol was achieved in high overall yield from (-)-D-tartaric acid. Key features include an FeCl3 mediated THF formation with very high selectivity. Synthesis of natural gonithalesdiol and its analogue 2,5-bis-epi-goniothalesdiol was achieved from a common intermediate.

  DOI：

  10.1021/jo060159f

文献信息

• Stereoselective Synthesis of (+)-Goniothalesdiol
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo060159f

  日期：2006.4.1

  Stereoselective synthesis of antitumor tetrahydrofuran (+)-goniothalesdiol was achieved in high overall yield from (-)-D-tartaric acid. Key features include an FeCl3 mediated THF formation with very high selectivity. Synthesis of natural gonithalesdiol and its analogue 2,5-bis-epi-goniothalesdiol was achieved from a common intermediate.
• 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.