glucose per-O-sulfate | 733705-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: glucose per-O-sulfate
• 英文别名: glucose sulfonic acid；[(2R,3R,4S,5R)-3,4,5,6-tetrasulfooxyoxan-2-yl]methyl hydrogen sulfate
• CAS: 733705-54-9
• 化学式: C₆H₁₂O₂₁S₅
• 分子量: 580.479
• InChiKey: RRZOMYHUSSAQTC-GASJEMHNSA-N

物化性质

• 密度：
  2.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  369
• 氢给体数：
  5
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  D-葡萄糖 在 氯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以78%的产率得到glucose per-O-sulfate
  参考文献：
  名称：

  The first example of glucose-containing Brønsted acid synthesis and catalysis: efficient synthesis of tetrahydrobenzo[α]xanthens and tetrahydrobenzo[α]acridines in water

  摘要：

  Glucose sulfonic acid (GSA) was synthesized for the first time and used as an efficient catalyst for the preparation of tetrahydrobenzo[alpha]xanthens and tetrahydrobenzo[alpha]acridines via the reaction of aromatic aldehydes, 2-naphthol (or beta-naphthylamine), and dimedone in water. Up to four new bonds and one new ring were formed in one-pot with water as the only by-product in these two reactions. The work opens up a new and efficient synthesis and application of sugar-containing Bronsted acid. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.029
• 作为试剂：
  描述：

  5,5-二甲基-1,3-环己二酮 、 邻甲氧基苯甲醛 、 2-萘酚 在 glucose per-O-sulfate 作用下， 以 水 为溶剂， 反应 4.0h， 以81%的产率得到12-(2-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  The first example of glucose-containing Brønsted acid synthesis and catalysis: efficient synthesis of tetrahydrobenzo[α]xanthens and tetrahydrobenzo[α]acridines in water

  摘要：

  Glucose sulfonic acid (GSA) was synthesized for the first time and used as an efficient catalyst for the preparation of tetrahydrobenzo[alpha]xanthens and tetrahydrobenzo[alpha]acridines via the reaction of aromatic aldehydes, 2-naphthol (or beta-naphthylamine), and dimedone in water. Up to four new bonds and one new ring were formed in one-pot with water as the only by-product in these two reactions. The work opens up a new and efficient synthesis and application of sugar-containing Bronsted acid. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.029

文献信息

• The first example of glucose-containing Brønsted acid synthesis and catalysis: efficient synthesis of tetrahydrobenzo[α]xanthens and tetrahydrobenzo[α]acridines in water
  作者：Yu Wan、Xiao-xiao Zhang、Chao Wang、Ling-ling Zhao、Liang-feng Chen、Gui-xiang Liu、Shu-ying Huang、Shu-ning Yue、Wen-li Zhang、Hui Wu

  DOI：10.1016/j.tet.2013.03.029

  日期：2013.5

  Glucose sulfonic acid (GSA) was synthesized for the first time and used as an efficient catalyst for the preparation of tetrahydrobenzo[alpha]xanthens and tetrahydrobenzo[alpha]acridines via the reaction of aromatic aldehydes, 2-naphthol (or beta-naphthylamine), and dimedone in water. Up to four new bonds and one new ring were formed in one-pot with water as the only by-product in these two reactions. The work opens up a new and efficient synthesis and application of sugar-containing Bronsted acid. (C) 2013 Elsevier Ltd. All rights reserved.