[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R,3S,4S)-2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-hydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]oxan-2-yl]methyl acetate | 908855-85-6

• 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: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R,3S,4S)-2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-hydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 908855-85-6
• 化学式: C₅₃H₈₈O₁₆Si₄
• 分子量: 1093.61
• InChiKey: URACKVIGRDKWJE-GNSBKJDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.86
• 重原子数：
  73
• 可旋转键数：
  24
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R,3S,4S)-2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-hydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]oxan-2-yl]methyl acetate 在 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.5h， 以82%的产率得到5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside
  参考文献：
  名称：

  Novel and Efficient Synthesis of Cyanidin 3-O-β-d-Glucoside from (+)-Catechin via a Flav-3-en-3-ol as a Key Intermediate

  摘要：

  A novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside (1) was accomplished the first time by a biomimetic oxidation route. From (+)-catechin, 3-OH was glucosylated, and the 4-position of the nucleus was then oxidized and dehydrated to give the 5,7,3', 4'-tetra-O-(tertbutyldimethylsilyl) flav-3-en-3-ol-3-O-glucoside (8) as a key intermediate. 8 was deprotected and oxidized under air in hydrogen chloride-MeOH to give 1.

  DOI：

  10.1021/ol0614976
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-yl]oxy]oxan-2-yl]methyl acetate 在 palladium dihydroxide 咪唑 、 4-二甲氨基吡啶 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~65.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R,3S,4S)-2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4-hydroxy-3,4-dihydro-2H-chromen-3-yl]oxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Novel and Efficient Synthesis of Cyanidin 3-O-β-d-Glucoside from (+)-Catechin via a Flav-3-en-3-ol as a Key Intermediate

  摘要：

  A novel and efficient synthesis of cyanidin 3-O-beta-D-glucoside (1) was accomplished the first time by a biomimetic oxidation route. From (+)-catechin, 3-OH was glucosylated, and the 4-position of the nucleus was then oxidized and dehydrated to give the 5,7,3', 4'-tetra-O-(tertbutyldimethylsilyl) flav-3-en-3-ol-3-O-glucoside (8) as a key intermediate. 8 was deprotected and oxidized under air in hydrogen chloride-MeOH to give 1.

  DOI：

  10.1021/ol0614976