(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[(2S,3R)-3-cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyrylaminooxy]-tetrahydro-pyran-2-carboxylic acid methyl ester | 319926-23-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[(2S,3R)-3-cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyrylaminooxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3R)-3-(cyclopentylmethyl)-4-oxo-4-piperidin-1-yl-2-[(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)methyl]butanoyl]amino]oxyoxane-2-carboxylate
• CAS: 319926-23-3
• 化学式: C₃₅H₅₂N₄O₁₄
• 分子量: 752.816
• InChiKey: HZOZOSYAJSGRIB-TYWUKLHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  214
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[(2S,3R)-3-cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyrylaminooxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 在 甲醇 、 sodium hydroxide 、 sodium methylate 作用下， 生成 (2S,3S,4S,5R,6S)-6-[(2S,3R)-3-Cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyrylaminooxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  The synthesis of the glucuronide adduct of Trocade™

  摘要：

  The synthetic preparation of the glucuronide adduct of Trocade(TM), a selective inhibitor of the MMP collagenase, is described. This was achieved by preparation of the protected O-glucuronsyl hydroxylamine (9) and subsequent coupling to the available carboxylic acid (7), followed by deprotection. The synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade(TM) occurs on the oxygen of the hydroxamic acid. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01556-2
• 作为产物：
  描述：

  乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 四丁基硫酸氢铵 、 碳酸氢钠 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[(2S,3R)-3-cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyrylaminooxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The synthesis of the glucuronide adduct of Trocade™

  摘要：

  The synthetic preparation of the glucuronide adduct of Trocade(TM), a selective inhibitor of the MMP collagenase, is described. This was achieved by preparation of the protected O-glucuronsyl hydroxylamine (9) and subsequent coupling to the available carboxylic acid (7), followed by deprotection. The synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade(TM) occurs on the oxygen of the hydroxamic acid. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01556-2