5-O-acetyl-1,4-anhydro-6-thio-D-glucitol | 321852-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 5-O-acetyl-1,4-anhydro-6-thio-D-glucitol
• 英文别名: [(1S)-1-[(2S,3R,4S)-3,4-dihydroxyoxolan-2-yl]-2-sulfanylethyl] acetate
• CAS: 321852-48-6
• 化学式: C₈H₁₄O₅S
• 分子量: 222.262
• InChiKey: GDHMUGOPXBCNHK-LXGUWJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-硝基苯甲酰氯 、 5-O-acetyl-1,4-anhydro-6-thio-D-glucitol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到5-O-acetyl-1,4-anhydro-2,3-di-O-p-nitrobenzoyl-6-S-p-nitrobenzoyl-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
• 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 作用下， 以 吡啶 为溶剂， 反应 0.5h， 以64%的产率得到5-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