2',3',4',6',2'',3'',4'',6''-octa O-acetyl-3,19-di-O-β-D-glucopyranosylandrographolide | 953081-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3',4',6',2'',3'',4'',6''-octa O-acetyl-3,19-di-O-β-D-glucopyranosylandrographolide
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(1R,2R,4aS,5R,8aS)-5-[(2E)-2-[(4S)-4-hydroxy-2-oxooxolan-3-ylidene]ethyl]-1,4a-dimethyl-6-methylidene-2-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 953081-50-0
• 化学式: C₄₈H₆₆O₂₃
• 分子量: 1011.04
• InChiKey: WLTBYPCYRBZVIO-MUQPOZAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  71
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  294
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2',3',4',6',2'',3'',4'',6''-octa O-acetyl-3,19-di-O-β-D-glucopyranosylandrographolide 在 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 3,19-di-O-β-D-glucopyranosylandrographolide
  参考文献：
  名称：

  ESIMS and NMR studies on the selective deprotection of acetylated glucosides by dibutyltin oxide

  摘要：

  The reaction process for the selective deprotection of acetylated glucosides by dibutyltin oxide in methanol is investigated by using methyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside as a model substrate with ESIMS and NMR techniques. According to the results, it is inferred that at first, dimeric 1,3-dimethoxytetrabutyldistannoxane is formed by the reaction of dibutyltin oxide with methanol, and then the tetraorganodistannoxane reacts with the acetylated glucoside to produce glucoside-organotin complex intermediates. Finally, the complex intermediates are hydrolyzed leading to the free-OH glucoside and organotin acetate derivatives. The reaction is affected by neighboring group participation and steric hindrance, which allow for high selectivities among different acetyl groups in acetylated glucosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.11.018