7-benzyloxy-2-(4-benzyloxyphenyl)-5-hydroxy-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-benzyloxy-2-(4-benzyloxyphenyl)-5-hydroxy-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one
• 英文别名: 5-hydroxy-7-phenylmethoxy-2-(4-phenylmethoxyphenyl)-6-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]chromen-4-one
• 化学式: C₆₃H₅₆O₁₀
• 分子量: 973.132
• InChiKey: MJLULROVRJQOKB-SSWNJRQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  73
• 可旋转键数：
  21
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-2-(4-benzyloxyphenyl)-5-hydroxy-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 在 palladium dihydroxide 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 异牡荆黄素
  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-[6-hydroxy-2,4-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 在 水 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以98.0 mg的产率得到7-benzyloxy-2-(4-benzyloxyphenyl)-5-hydroxy-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-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

文献信息

• Mahling, Juergen-Andreas; Jung, Karl-Heinz; Schmidt, Richard R., Liebigs Annalen, 1995, # 3, p. 461 - 466
  作者：Mahling, Juergen-Andreas、Jung, Karl-Heinz、Schmidt, Richard R.

  DOI：——

  日期：——
• 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.