(2R,3S,4R,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(acetoxymethyl)-6-((1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate | 1360440-95-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(acetoxymethyl)-6-((1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS: 1360440-95-4
• 化学式: C₄₃H₄₃NO₁₄
• 分子量: 797.813
• InChiKey: MNDCBYSGRREYBW-FOQHIHNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  58.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  210.29
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(acetoxymethyl)-6-((1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以74%的产率得到2-(1-(((2R,3R,4R,5S,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-methylpent-3-en-1-yl)-5,8-dihydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

  摘要：

  The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.143
• 作为产物：
  描述：

  2-氨基-2-脱氧葡萄糖盐酸盐 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 肼 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3S,4R,5R,6R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-(acetoxymethyl)-6-((1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin

  摘要：

  The N-acetyl glucosaminosides of shikonin/alkannin were synthesized by chemical glycosylation, which provided an ideal approach to resolve the mixture of enantiomeric shikonin and alkannin co-existed in the Chinese herbs. The glycosylated shikonin and alkannin exhibited stronger binding activity to human telomeric G-quadruplex DNA than their parent structures. This research indicated that glycosylation of natural product with amino sugars is an effective strategy to improve their DNA-binding affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.143