1-(4-(benzyloxy)phenyl)-3-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)propane-1,3-dione | 1154756-99-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(4-(benzyloxy)phenyl)-3-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)propane-1,3-dione
• 英文别名: 1-[2-hydroxy-4,6-bis(phenylmethoxy)-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenyl]-3-(4-phenylmethoxyphenyl)propane-1,3-dione
• CAS: 1154756-99-6
• 化学式: C₇₀H₆₄O₁₁
• 分子量: 1081.27
• InChiKey: SUCFJINVKSWNOB-MMPRHHSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  81
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(4-(benzyloxy)phenyl)-3-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)propane-1,3-dione 在 Amberlyst 15 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 72.0h， 以58%的产率得到5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-8-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-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
• 作为产物：
  描述：

  (1H-benzo[d][1,2,3]triazol-1-yl)[4-(benzyloxy)phenyl]methanone 、 1-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)ethanone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以95%的产率得到1-(4-(benzyloxy)phenyl)-3-(4,6-bis(benzyloxy)-2-hydroxy-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

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.