(S)-N-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide | 1192721-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-N-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide
• 英文别名: (3S)-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydro-1,4-benzodioxine-3-carboxamide
• CAS: 1192721-94-0
• 化学式: C₁₅H₁₉NO₈
• 分子量: 341.318
• InChiKey: CUDAQZHMNPPXIF-RGOPTCMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((S)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamido)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium methylate 、 Amberlist 15 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以75%的产率得到(S)-N-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide
  参考文献：
  名称：

  Synthesis and glycogen phosphorylase inhibitory activity of N-(β-d-glucopyranosyl)amides possessing 1,4-benzodioxane moiety

  摘要：

  A series of N-(beta-D-glucopyranosyl)amides 5d-i were synthesized by PMe3 mediated Staudinger reaction of O-peracetylated beta-D-glucopyranosyl azide (1) followed by acylation with carboxylic acids 3d-i and subsequent Zemplen deacetylation. The new compounds were tested for their inhibitory activity against rabbit muscle glycogen phosphorylase and the structure-activity relationships of these compounds are also discussed in this paper. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.052