(2S,3S,4S,5R,6S)-6-[(6-{[5-(benzyloxycarbonyl)-5-methylhexyl]oxy}-2,2-dimethylhexanoyl)oxy]-3,4,5-trihydroxytetrahydropyran-2-carboxylic acid methyl ester | 863292-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6S)-6-[(6-{[5-(benzyloxycarbonyl)-5-methylhexyl]oxy}-2,2-dimethylhexanoyl)oxy]-3,4,5-trihydroxytetrahydropyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,4S,5R,6S)-6-[6-(5,5-dimethyl-6-oxo-6-phenylmethoxyhexoxy)-2,2-dimethylhexanoyl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 863292-18-6
• 化学式: C₃₀H₄₆O₁₁
• 分子量: 582.689
• InChiKey: HFGXMMYCSBESMJ-AMWBNRJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  41
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-6-[(6-{[5-(benzyloxycarbonyl)-5-methylhexyl]oxy}-2,2-dimethylhexanoyl)oxy]-3,4,5-trihydroxytetrahydropyran-2-carboxylic acid methyl ester 在 Candida antarctica lipase B 、 phosphate buffer 作用下， 以 异丙醇 为溶剂， 反应 8.5h， 以85%的产率得到(2S,3S,4S,5R,6S)-6-[(6-{[5-(benzyloxycarbonyl)-5-methylhexyl]oxy}-2,2-dimethylhexanoyl)oxy]-3,4,5-trihydroxytetrahydropyran-2-carboxylic acid
  参考文献：
  名称：

  Preparation of CI‐1027 Glucuronide: Metabolite of a Remarkable Lipid‐Modulating Agent

  摘要：

  The preparation of the 1 beta-glucuronide of the diacid, CI-1027, is described. The key synthetic steps are coupling of the mono-protected acid with bromoglucuronide, deacetylation, and enzymatic hydrolysis.

  DOI：

  10.1081/scc-200061648
• 作为产物：
  描述：

  D-吡喃葡萄糖醛酸 在 吡啶 、 甲醇 、 氢溴酸 、 碘 、 溶剂黄146 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 63.0h， 生成 (2S,3S,4S,5R,6S)-6-[(6-{[5-(benzyloxycarbonyl)-5-methylhexyl]oxy}-2,2-dimethylhexanoyl)oxy]-3,4,5-trihydroxytetrahydropyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Preparation of CI‐1027 Glucuronide: Metabolite of a Remarkable Lipid‐Modulating Agent

  摘要：

  The preparation of the 1 beta-glucuronide of the diacid, CI-1027, is described. The key synthetic steps are coupling of the mono-protected acid with bromoglucuronide, deacetylation, and enzymatic hydrolysis.

  DOI：

  10.1081/scc-200061648

文献信息

• Preparation of CI‐1027 Glucuronide: Metabolite of a Remarkable Lipid‐Modulating Agent
  作者：Anne Akin、Timothy T. Curran

  DOI：10.1081/scc-200061648

  日期：2005.6.1

  The preparation of the 1 beta-glucuronide of the diacid, CI-1027, is described. The key synthetic steps are coupling of the mono-protected acid with bromoglucuronide, deacetylation, and enzymatic hydrolysis.