β-D-glucopyranosyl dibutyl phosphoramidate | 1240498-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranosyl dibutyl phosphoramidate
• 英文别名: (2R,3R,4S,5S,6R)-2-(dibutoxyphosphorylamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1240498-30-9
• 化学式: C₁₄H₃₀NO₈P
• 分子量: 371.368
• InChiKey: PKSRGEDAAFJXEV-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  β-D-glucopyranosyl dibutyl phosphoramidate 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 碳酸氢钠 、 potassium bromide 作用下， 以 水 、 乙腈 为溶剂， 以55%的产率得到β-D-glucuronyl dibutyl phosphoramidate
  参考文献：
  名称：

  Straightforward synthesis of novel Akt inhibitors based on a glucose scaffold

  摘要：

  Glucose-based analogues of phosphatidylinositol 3-phosphate were straightforwardly synthesised from 2,3,4,6-tetra-O-acetyl-D-glucosyl bromide as protein kinase B (PKB/Akt) inhibitors. beta-D-Glucuronyl diethyl phosphoramidate was identified as a promising hit through biological screening in two different cellular systems. In addition, RNA interference experiments (siRNA) provide evidence of the ability of the compound to exert biological effects specifically through Akt signalling. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.013
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl dibutyl phosphoramidate 在 甲醇 、 sodium 作用下， 以90%的产率得到β-D-glucopyranosyl dibutyl phosphoramidate
  参考文献：
  名称：

  Straightforward synthesis of novel Akt inhibitors based on a glucose scaffold

  摘要：

  Glucose-based analogues of phosphatidylinositol 3-phosphate were straightforwardly synthesised from 2,3,4,6-tetra-O-acetyl-D-glucosyl bromide as protein kinase B (PKB/Akt) inhibitors. beta-D-Glucuronyl diethyl phosphoramidate was identified as a promising hit through biological screening in two different cellular systems. In addition, RNA interference experiments (siRNA) provide evidence of the ability of the compound to exert biological effects specifically through Akt signalling. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.12.013

文献信息

• Straightforward synthesis of novel Akt inhibitors based on a glucose scaffold
  作者：Laura Cipolla、Cristina Redaelli、Francesca Granucci、Giuseppe Zampella、Antonio Zaza、Riccardo Chisci、Francesco Nicotra

  DOI：10.1016/j.carres.2009.12.013

  日期：2010.7

  Glucose-based analogues of phosphatidylinositol 3-phosphate were straightforwardly synthesised from 2,3,4,6-tetra-O-acetyl-D-glucosyl bromide as protein kinase B (PKB/Akt) inhibitors. beta-D-Glucuronyl diethyl phosphoramidate was identified as a promising hit through biological screening in two different cellular systems. In addition, RNA interference experiments (siRNA) provide evidence of the ability of the compound to exert biological effects specifically through Akt signalling. (C) 2009 Elsevier Ltd. All rights reserved.