2-O-(p-toluenesulfonyl)sucrose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-(p-toluenesulfonyl)sucrose
• 英文别名: Tos(-2)Glc(a1-2b)Fruf；[(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 4-methylbenzenesulfonate
• 化学式: C₁₉H₂₈O₁₃S
• 分子量: 496.49
• InChiKey: SNMMFBKNJZYWQQ-ZSOARRGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  221
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  1-对甲基苯磺酰咪唑 、 蔗糖 在 molecular sieve 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2160.0h， 以38%的产率得到2-O-(p-toluenesulfonyl)sucrose
  参考文献：
  名称：

  Direct regioselective 2-O-(p-toluenesulfonylation) of sucrose

  摘要：

  2-O-(p-Toluenesulfonyl)sucrose was regioselectively synthesized by direct p-toluenesulfonylation of sucrose using N-(p-toluenesulfonyl)imidazole in the presence of molecular sieves at 40degreesC. The reactivities of the sucrose hydroxy groups toward this sulfonylation increased in the order as follows: OH-2 much greater than OH-1' > OH-3' > OH-6 > OH-6'. These results were diametrically opposite to the expected sulfonylation with p-toluenesulfonyl chloride in pyridine. for which the reactivity increased in the order as follows: OH-6', OH-6 much greater than OH-1' > OH-2. The desired 2-O-(p-toluenesulfonyl)sucrose was readily isolated by simple open reversed-phase column chromatography. followed by recrystallization, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00039-3

文献信息

• Direct regioselective 2-O-(p-toluenesulfonylation) of sucrose
  作者：Katsunori Teranishi

  DOI：10.1016/s0008-6215(02)00039-3

  日期：2002.4

  2-O-(p-Toluenesulfonyl)sucrose was regioselectively synthesized by direct p-toluenesulfonylation of sucrose using N-(p-toluenesulfonyl)imidazole in the presence of molecular sieves at 40degreesC. The reactivities of the sucrose hydroxy groups toward this sulfonylation increased in the order as follows: OH-2 much greater than OH-1' > OH-3' > OH-6 > OH-6'. These results were diametrically opposite to the expected sulfonylation with p-toluenesulfonyl chloride in pyridine. for which the reactivity increased in the order as follows: OH-6', OH-6 much greater than OH-1' > OH-2. The desired 2-O-(p-toluenesulfonyl)sucrose was readily isolated by simple open reversed-phase column chromatography. followed by recrystallization, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. (C) 2002 Elsevier Science Ltd. All rights reserved.