1,6-di-S-acetyl-2,5-anhydro-1,6-dithio-L-iditol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,6-di-S-acetyl-2,5-anhydro-1,6-dithio-L-iditol
• 英文别名: S-[[(2R,3S,4S,5R)-5-(acetylsulfanylmethyl)-3,4-dihydroxyoxolan-2-yl]methyl] ethanethioate
• 化学式: C₁₀H₁₆O₅S₂
• 分子量: 280.366
• InChiKey: YAQMCTPCCKHGBX-AXTSPUMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  山梨醇 、 硫代乙酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 silica gel 作用下， 以 吡啶 、 乙醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 以41%的产率得到3-O-acetyl-1,4-anhydro-6-thio-D-glucitol
  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.