1,6-di-S-acetyl-2,5-anhydro-3,4-di-O-p-nitrobenzoyl-1,6-dithio-D-glucitol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-di-S-acetyl-2,5-anhydro-3,4-di-O-p-nitrobenzoyl-1,6-dithio-D-glucitol
• 英文别名: [(2S,3S,4S,5R)-2,5-bis(acetylsulfanylmethyl)-4-(4-nitrobenzoyl)oxyoxolan-3-yl] 4-nitrobenzoate
• 化学式: C₂₄H₂₂N₂O₁₁S₂
• 分子量: 578.577
• InChiKey: PEFCTFUCKBKDLB-CIAFKFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  甘露醇 、 4-硝基苯甲酰氯 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 吡啶 作用下， 以 吡啶 为溶剂， 反应 5.5h， 生成 1,6-di-S-acetyl-2,5-anhydro-3,4-di-O-p-nitrobenzoyl-1,6-dithio-D-glucitol 、 2,5-di-O-acetyl-3,4-di-O-p-nitrobenzoyl-1,6-di-S-p-nitrobenzoyl-1,6-dithio-D-mannitol
  参考文献：
  名称：

  The thio-Mitsunobu reaction of d-glucitol, d-mannitol, galactitol and 1-seleno-d-xylitol

  摘要：

  Unprotected D-glucitol is transformed into 5-O-acetyl-1,4-anhydro-6-thio-D-glucitol (3) in one step by use of the thio-Mitsunobu reaction. Rearrangement (acetyl group migration) to form 3-O-acetyl-1,4-anhydro-6-thio-D-glucitol occurs during column chromatography of 3 on silica gel. 2,5-Di-O-acetyl-1,6-dithio-D-mannitol and 1,6-di-S-acetyl-2,5-anhydro-1,6-dithio-D-glucitol, (characterized as the corresponding p-nitrobenzoates) are formed from D-mannitol, whereas galactitol yields a mass of unidentified products. 1-Seleno-D-xylitol, produced by reduction of D-xylose with hydrogen selenide, does not undergo a Mitsunobu reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00233-0

文献信息

• The thio-Mitsunobu reaction of d-glucitol, d-mannitol, galactitol and 1-seleno-d-xylitol
  作者：Oliver Schulze、Stefan Bruns、Jürgen Voss、Gunadi Adiwidjaja

  DOI：10.1016/s0008-6215(00)00233-0

  日期：2000.12

  Unprotected D-glucitol is transformed into 5-O-acetyl-1,4-anhydro-6-thio-D-glucitol (3) in one step by use of the thio-Mitsunobu reaction. Rearrangement (acetyl group migration) to form 3-O-acetyl-1,4-anhydro-6-thio-D-glucitol occurs during column chromatography of 3 on silica gel. 2,5-Di-O-acetyl-1,6-dithio-D-mannitol and 1,6-di-S-acetyl-2,5-anhydro-1,6-dithio-D-glucitol, (characterized as the corresponding p-nitrobenzoates) are formed from D-mannitol, whereas galactitol yields a mass of unidentified products. 1-Seleno-D-xylitol, produced by reduction of D-xylose with hydrogen selenide, does not undergo a Mitsunobu reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.