1-O-tosyl-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose | 1357160-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-tosyl-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose
• CAS: 1357160-39-4
• 化学式: C₄₂H₄₄O₉S
• 分子量: 724.872
• InChiKey: MGAFEVKMWDTJEY-DJLQKWJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  52.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-O-tosyl-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 在 甲醇 、 potassium carbonate 、 三氟乙酸 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0~100.0 ℃ 、206.85 kPa 条件下， 反应 3.5h， 生成 (5S,7R,8S,9S,10R)-8,9,10-trihydroxy-7-(hydroxymethyl)-N-(4-methoxyphenyl)-6-oxa-2-thia-1,3-diazaspiro[4.5]decane-2,2-dioxide
  参考文献：
  名称：

  Synthesis of N-aryl spiro-sulfamides as potential glycogen phosphorylase inhibitors

  摘要：

  A new C-glucosylated spiro-sulfamide has been prepared and evaluated toward glycogen phosphorylase inhibition. The synthesis was carried out successfully by nucleophilic displacement of 1-O-tosyl or 1-deoxy-1-iodo-alpha-D-gluco-hept-2-ulopyranose tetra-O-benzylated derivative using aryl amines. followed by the formation of the corresponding cyclic sulfamide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.049
• 作为产物：
  描述：

  3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以86%的产率得到1-O-tosyl-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose
  参考文献：
  名称：

  Synthesis of N-aryl spiro-sulfamides as potential glycogen phosphorylase inhibitors

  摘要：

  A new C-glucosylated spiro-sulfamide has been prepared and evaluated toward glycogen phosphorylase inhibition. The synthesis was carried out successfully by nucleophilic displacement of 1-O-tosyl or 1-deoxy-1-iodo-alpha-D-gluco-hept-2-ulopyranose tetra-O-benzylated derivative using aryl amines. followed by the formation of the corresponding cyclic sulfamide. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.049