(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1192721-69-9

• 分子结构分类: 有机化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1192721-69-9
• 化学式: C₂₃H₂₇NO₁₂
• 分子量: 509.467
• InChiKey: NXACFNKSYTWPRS-ZFVIQDPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  161.99
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,3-dihydrobenzo[b][1,4]dioxine-6-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95%的产率得到N-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-2,3-dihydrobenzo[b][1,4]dioxine-6-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
• 作为产物：
  描述：

  2,3-二氢-1,4-苯并二噁烷-6-羧酸 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 在 三甲基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 54.0h， 以69%的产率得到(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  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