(2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran | 887927-64-2

• 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)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran
• 英文别名: [(2S,3R,4R,5R)-2-but-3-enyl-4-[tert-butyl(dimethyl)silyl]oxy-5-phenyloxolan-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 887927-64-2
• 化学式: C₂₆H₄₆O₃Si₂
• 分子量: 462.82
• InChiKey: PNYWTUOKGQLWOL-OLKYXYMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.87
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran 、 甲醇 在 碳酸氢钠 、 臭氧 、 4-二甲氨基吡啶 、 乙酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 以66%的产率得到methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate
  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
• 作为产物：
  描述：

  (S)-((4S,5R)-5-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methyl 4-methylbenzenesulfonate 在 吡啶 、 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 (2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran
  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.