(2S,3R,4R,5R,6R)-5-(((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)thio)-2-methoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl diacetate | 870192-86-2

• 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,3R,4R,5R,6R)-5-(((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)thio)-2-methoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS: 870192-86-2
• 化学式: C₂₃H₃₂O₁₆S
• 分子量: 596.563
• InChiKey: ODPJQYPWAWSDGW-DNAURDFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.38
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  205.72
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R,6R)-5-(((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)thio)-2-methoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl diacetate 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hydroxide 、 碘苯二乙酸 、 三乙基硅基三氟甲磺酸酯 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 生成 (2S,3R,4S,5R,6S)-6-[(2S,3R,4R,5R,6R)-2-carboxy-6-[(2R,3R,4R,5R,6S)-2-carboxy-4,5-dihydroxy-6-methoxyoxan-3-yl]sulfanyl-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

  摘要：

  A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.019
• 作为产物：
  描述：

  methyl 2,3-di-O-acetyl-α-D-glucopyranoside 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 (2S,3R,4R,5R,6R)-5-(((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-hydroxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)thio)-2-methoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Design, synthesis, and enzymatic property of a sulfur-substituted analogue of trigalacturonic acid

  摘要：

  A sulfur-substituted analogue of trigalacturonic acid (3) was synthesized. The synthesis features the application of 3-cyano-3-(tert-butyldimethylsilyl)oxypropylthioether (CSP) as a novel protective group for thiols. This analogue was designed with the expectation that it would be a stable analogous substrate for endo-polygalacturonase isolated from Stereum purpureum based on computer modeling experiments. Surface plasmon resonance experiments revealed that 3 forms a stable complex with the target enzyme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.019