(S)-5-((4R,5R)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one | 944352-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-((4R,5R)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one
• 英文别名: (2S)-2-[(4R,5R)-5-[(R)-hydroxy(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2H-furan-5-one
• CAS: 944352-99-2
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: UZDJOZQDGLVRGS-ZGKBOVNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-5-((4R,5R)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以70%的产率得到7-C-Phenyl-D-gluco-hept-2-enono-γ-lactone
  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：

  在 吡啶 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以0.1 g的产率得到(S)-5-((4R,5R)-5-((R)-hydroxy(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one
  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.