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 | 1064179-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 1-[6-[tert-butyl(diphenyl)silyl]oxy-2,4-bis(phenylmethoxy)-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenyl]ethanone
• CAS: 1064179-48-1
• 化学式: C₇₂H₇₂O₉Si
• 分子量: 1109.44
• InChiKey: KHKKLEJJZHGNCT-YWQVVBDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  82
• 可旋转键数：
  26
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1H-benzo[d][1,2,3]triazol-1-yl)[4-(benzyloxy)phenyl]methanone 、 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 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以68%的产率得到1-[4-(benzyloxy)phenyl]-3-{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}propane-1,3-dione
  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：

  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

文献信息

• Concise Synthesis of Chafurosides A and B
  作者：Takumi Furuta、Miho Nakayama、Hirotaka Suzuki、Hiroko Tajimi、Makoto Inai、Haruo Nukaya、Toshiyuki Wakimoto、Toshiyuki Kan

  DOI：10.1021/ol900689m

  日期：2009.6.4

  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.