1-(4-(benzyloxy)-6-((tert-butyldiphenylsilyl)oxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenyl)ethan-1-one | 1064179-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(benzyloxy)-6-((tert-butyldiphenylsilyl)oxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenyl)ethan-1-one
• CAS: 1064179-44-7
• 化学式: C₆₅H₆₆O₉Si
• 分子量: 1019.32
• InChiKey: ODEKREWSSQOOJI-WZGJHNJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.53
• 重原子数：
  75.0
• 可旋转键数：
  22.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(4-(benzyloxy)-6-((tert-butyldiphenylsilyl)oxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenyl)ethan-1-one 、 苯甲醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到1-{2,4-bis(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]phenyl}ethanone
  参考文献：
  名称：

  Concise Synthesis of Chafurosides A and B

  摘要：

  The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from beta-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.

  DOI：

  10.1021/ol900689m
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 、 1-{4-(benzyloxy)-2,6-dihydroxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl]phenyl}ethanone 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以95%的产率得到1-(4-(benzyloxy)-6-((tert-butyldiphenylsilyl)oxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenyl)ethan-1-one
  参考文献：
  名称：

  Concise Synthesis of Chafurosides A and B

  摘要：

  The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from beta-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.

  DOI：

  10.1021/ol900689m