1-deoxy-1-amino-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose | 1357160-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-amino-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose
• 英文别名: (2S,3R,4S,5R,6R)-2-(aminomethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 1357160-41-8
• 化学式: C₃₅H₃₉NO₆
• 分子量: 569.698
• InChiKey: WNZYNXOTFCUSHP-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-amino-3,4,5,7-tetra-O-benzyl-D-gluco-hept-2-ulopyranose 、 tert-butyl (N-triethylammonium sulfonyl)carbamate 以 四氢呋喃 为溶剂， 反应 21.0h， 以68%的产率得到(5S,7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-(benzyloxymethyl)-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 在 4-二甲氨基吡啶 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 20.0~100.0 ℃ 、413.7 kPa 条件下， 反应 20.5h， 生成 1-deoxy-1-amino-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

文献信息

• Synthesis of N-aryl spiro-sulfamides as potential glycogen phosphorylase inhibitors
  作者：Tony Tite、Loic Tomas、Tibor Docsa、Pal Gergely、José Kovensky、David Gueyrard、Anne Wadouachi

  DOI：10.1016/j.tetlet.2011.12.049

  日期：2012.2

  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.