(2S,3R,4S,5S,6R)-2-[(R)-2-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2H-chromen-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol | 908855-87-8

• 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: (2S,3R,4S,5S,6R)-2-[(R)-2-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2H-chromen-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS: 908855-87-8
• 化学式: C₄₅H₇₈O₁₁Si₄
• 分子量: 907.45
• InChiKey: JMQDHONSIDLHCC-NIIOQGPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.51
• 重原子数：
  60.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  145.53
• 氢给体数：
  4.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6R)-2-[(R)-2-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2H-chromen-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以32 mg的产率得到cyanidin-3-O-β-D-glucopyranoside trifluoroacetic acid salt
  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：

  5,7,3',4'-tetra-O-(tert-butyldimethylsilyl)flav-3-en-3-ol 3-O-glucoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82%的产率得到(2S,3R,4S,5S,6R)-2-[(R)-2-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2H-chromen-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
  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