((S)-1-((4S,5R)-5-((S)-1-(benzyloxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)-tert-butyldimethylsilane | 944353-00-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((S)-1-((4S,5R)-5-((S)-1-(benzyloxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)-tert-butyldimethylsilane
• 英文别名: tert-butyl-[(S)-[(4S,5R)-2,2-dimethyl-5-[(1S)-1-phenylmethoxypent-4-enyl]-1,3-dioxolan-4-yl]-phenylmethoxy]-dimethylsilane
• CAS: 944353-00-8
• 化学式: C₃₀H₄₄O₄Si
• 分子量: 496.762
• InChiKey: SSAIJGQWZLTYFS-YVHASNINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以94%的产率得到(4R,5R)-4-((S)-hydroxy(phenyl)methyl)-5-((S)-1-benzyloxypent-4-enyl)-2,2-dimethyl-1,3-dioxolane
  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：

  1-(S)-((4R,5S)-5-((S)-tert-butyldimethylsilyloxy(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-4-en-1-ol 、 溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以91%的产率得到((S)-1-((4S,5R)-5-((S)-1-(benzyloxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methoxy)-tert-butyldimethylsilane
  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