(S)-((4S,5R)-5-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methyl 4-methylbenzenesulfonate | 887927-62-0

• 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)-((4S,5R)-5-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methyl 4-methylbenzenesulfonate
• 英文别名: [(S)-[(4S,5R)-5-[(1S)-1-(methoxymethoxy)pent-4-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethyl] 4-methylbenzenesulfonate
• CAS: 887927-62-0
• 化学式: C₂₆H₃₄O₇S
• 分子量: 490.618
• InChiKey: WOXGDUMUGYCTCC-CXSMSNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 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 、 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 16.5h， 生成 (S)-((4S,5R)-5-((S)-1-(methoxymethoxy)pent-4-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)(phenyl)methyl 4-methylbenzenesulfonate
  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.