Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoylamino]-tetrahydro-pyran-4-yl ester | 201414-04-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoylamino]-tetrahydro-pyran-4-yl ester
• CAS: 201414-04-2
• 化学式: C₃₅H₄₅NO₁₁
• 分子量: 655.742
• InChiKey: GRFGXDNATPAIBP-BURWJUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoylamino]-tetrahydro-pyran-4-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以92%的产率得到(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]nona-2,4,6,8-tetraenamide
  参考文献：
  名称：

  N-linked glycoside/glucuronide conjugates of retinoids: acitretin

  摘要：

  Glucuronide conjugates of retinoids have been found to be active metabolites of the parent molecules. However, O-acylglucuronide retinoids are liable to hydrolysis and retinoid ring oxidation. We have prepared stable N-linked glycosides of acitretin in efforts to overcome these problems. The synthesis and preliminary biological studies of the analogs are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10140-8
• 作为产物：
  描述：

  1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 65.0h， 生成 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoylamino]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  N-linked glycoside/glucuronide conjugates of retinoids: acitretin

  摘要：

  Glucuronide conjugates of retinoids have been found to be active metabolites of the parent molecules. However, O-acylglucuronide retinoids are liable to hydrolysis and retinoid ring oxidation. We have prepared stable N-linked glycosides of acitretin in efforts to overcome these problems. The synthesis and preliminary biological studies of the analogs are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10140-8