3,4-(diphenylmethylendioxy)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid | 270061-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-(diphenylmethylendioxy)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid
• 英文别名: 2,2-diphenyl-7-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-1,3-benzodioxole-5-carboxylic acid
• CAS: 270061-97-7
• 化学式: C₅₄H₄₈O₁₀
• 分子量: 856.969
• InChiKey: ICXQDQRAFUYBND-NRFCZZEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.13
• 重原子数：
  64.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  111.14
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,4-(diphenylmethylendioxy)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以94%的产率得到gallic acid 3-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of antioxidative and anti-inflammatory drugs glucoconjugates

  摘要：

  Glucoconjugates of (+/-)-ibuprofen, (+/-)-alpha-tocopherol (vitamin E), gentisic acid, gallic acid, 2,6-bis(tert-butyl)-4-thiophenol, and N-acetyl-L-cysteine were prepared with the objective of increasing the bioavailability of such antioxidant and anti-inflammatory drugs. The O-glucosides were synthesized using benzylated alpha-D-glucopyranosyl trichloracetimidate as glycosyl donor. For the synthesis of the S-glucosides, the glycosyl donor 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose provided higher yields than the corresponding O-acetylated imidate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00311-0
• 作为产物：
  描述：

  ethyl 3,4-(diphenylmethylendioxy)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoate 在 氢氧化钾 作用下， 以 乙二醇二甲醚 为溶剂， 反应 20.0h， 以89%的产率得到3,4-(diphenylmethylendioxy)-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)benzoic acid
  参考文献：
  名称：

  Synthesis of antioxidative and anti-inflammatory drugs glucoconjugates

  摘要：

  Glucoconjugates of (+/-)-ibuprofen, (+/-)-alpha-tocopherol (vitamin E), gentisic acid, gallic acid, 2,6-bis(tert-butyl)-4-thiophenol, and N-acetyl-L-cysteine were prepared with the objective of increasing the bioavailability of such antioxidant and anti-inflammatory drugs. The O-glucosides were synthesized using benzylated alpha-D-glucopyranosyl trichloracetimidate as glycosyl donor. For the synthesis of the S-glucosides, the glycosyl donor 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose provided higher yields than the corresponding O-acetylated imidate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00311-0