(Z)-3(S),4(S),5(R)-triacetoxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-(p-toluenesulfonyloxy)-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid methyl ester | 1231185-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3(S),4(S),5(R)-triacetoxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-(p-toluenesulfonyloxy)-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid methyl ester
• 英文别名: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[3-methoxy-2-(4-methylphenyl)sulfonyloxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]oxane-2-carboxylate
• CAS: 1231185-00-4
• 化学式: C₃₈H₄₂O₁₇S
• 分子量: 802.807
• InChiKey: AZFPPCPSUGVZFW-QHZPMSOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  56
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  (Z)-3(S),4(S),5(R)-triacetoxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-(p-toluenesulfonyloxy)-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以62%的产率得到(Z)-3(S),4(S),5(R)-trihydroxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-hydroxy-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid
  参考文献：
  名称：

  Regio- and Stereospecific Synthesis of Mono-β-d-Glucuronic Acid Derivatives of Combretastatin A-1

  摘要：

  Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-D-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.

  DOI：

  10.1021/np100108e
• 作为产物：
  描述：

  [2-hydroxy-6-methoxy-3-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl] 4-methylbenzenesulfonate 、 乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.17h， 以35%的产率得到(Z)-3(S),4(S),5(R)-triacetoxy-6(S)-[(3,4,5-trimethoxy)-(4'-methoxy-3'-(p-toluenesulfonyloxy)-2'-stilbenyloxy)]tetrahydropyran-2(S)-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio- and Stereospecific Synthesis of Mono-β-d-Glucuronic Acid Derivatives of Combretastatin A-1

  摘要：

  Synthetic routes have been established for the preparation of regio- and stereoisomerically pure samples of the mono-beta-D-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.

  DOI：

  10.1021/np100108e