(S)-dihydro-5-((4R,5S)-5-((S)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3H-furan-2-one | 868761-59-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-dihydro-5-((4R,5S)-5-((S)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3H-furan-2-one
• 英文别名: (5S)-5-[(4R,5S)-5-[(S)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-2-one
• CAS: 868761-59-5
• 化学式: C₂₂H₃₄O₅Si
• 分子量: 406.594
• InChiKey: IIKGBJFXMHBGAH-IJXRJRJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-dihydro-5-((4R,5S)-5-((S)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3H-furan-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(S)-dihydro-5-((4R,5R)-5-((S)-hydroxy(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(3H)-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
• 作为产物：
  描述：

  (5S)-5-[(4R,5S)-5-[(S)-[tert-butyl(dimethyl)silyl]oxy-phenylmethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-2-ol 在 Celite 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以0.29 g的产率得到(S)-dihydro-5-((4R,5S)-5-((S)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-3H-furan-2-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