benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5S,6S)-2-(6-azidohexoxy)-3-benzoyloxy-5-phenylmethoxy-6-phenylmethoxycarbonyloxan-4-yl]oxy-5-benzoyloxy-2-(benzoyloxymethyl)-4-phenylmethoxyoxan-3-yl]oxy-5-benzoyloxy-4-hydroxy-3-phenylmethoxyoxane-2-carboxylate | 1352561-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5S,6S)-2-(6-azidohexoxy)-3-benzoyloxy-5-phenylmethoxy-6-phenylmethoxycarbonyloxan-4-yl]oxy-5-benzoyloxy-2-(benzoyloxymethyl)-4-phenylmethoxyoxan-3-yl]oxy-5-benzoyloxy-4-hydroxy-3-phenylmethoxyoxane-2-carboxylate
• CAS: 1352561-79-5
• 化学式: C₈₇H₈₅N₃O₂₂
• 分子量: 1524.64
• InChiKey: HDDRZYNVGOTVFB-WCIKXJOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  112
• 可旋转键数：
  42
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  276
• 氢给体数：
  1
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5S,6S)-2-(6-azidohexoxy)-3-benzoyloxy-5-phenylmethoxy-6-phenylmethoxycarbonyloxan-4-yl]oxy-5-benzoyloxy-2-(benzoyloxymethyl)-4-phenylmethoxyoxan-3-yl]oxy-5-benzoyloxy-4-hydroxy-3-phenylmethoxyoxane-2-carboxylate 在 potassium hydroxide 、 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 1,4-二氧六环 、 水 、 叔丁醇 为溶剂， 反应 144.0h， 以28%的产率得到(2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6S)-2-(6-aminohexoxy)-6-carboxy-3,5-dihydroxyoxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Exploring and Exploiting the Reactivity of Glucuronic Acid Donors

  摘要：

  The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic add esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiociisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.

  DOI：

  10.1021/jo201586r
• 作为产物：
  描述：

  benzyl (2S,3S,4S,5R,6R)-6-(6-azidohexoxy)-5-benzoyloxy-4-[(2S,3R,4S,5R,6R)-3-benzoyloxy-6-(benzoyloxymethyl)-5-[(2R,3R,4S,5S,6S)-3-benzoyloxy-4-(4-oxopentanoyloxy)-5-phenylmethoxy-6-phenylmethoxycarbonyloxan-2-yl]oxy-4-phenylmethoxyoxan-2-yl]oxy-3-phenylmethoxyoxane-2-carboxylate 在 吡啶 、 乙酸肼 、 溶剂黄146 作用下， 以93%的产率得到benzyl (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-6-[(2R,3R,4S,5S,6S)-2-(6-azidohexoxy)-3-benzoyloxy-5-phenylmethoxy-6-phenylmethoxycarbonyloxan-4-yl]oxy-5-benzoyloxy-2-(benzoyloxymethyl)-4-phenylmethoxyoxan-3-yl]oxy-5-benzoyloxy-4-hydroxy-3-phenylmethoxyoxane-2-carboxylate
  参考文献：
  名称：

  Exploring and Exploiting the Reactivity of Glucuronic Acid Donors

  摘要：

  The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic add esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiociisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.

  DOI：

  10.1021/jo201586r

文献信息

• Exploring and Exploiting the Reactivity of Glucuronic Acid Donors
  作者：Ana-Rae de Jong、Bas Hagen、Vincent van der Ark、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. Van der Marel

  DOI：10.1021/jo201586r

  日期：2012.1.6

  The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic add esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiociisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.