1-O-(2-benzyloxyethyl)-2-deoxy-3,4-di-O-benzoyl-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside | 1447811-16-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-(2-benzyloxyethyl)-2-deoxy-3,4-di-O-benzoyl-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-4-benzoyloxy-6-(2-phenylmethoxyethoxy)-5-[(2,2,2-trifluoroacetyl)amino]-2-[tri(propan-2-yl)silyloxymethyl]oxan-3-yl] benzoate
• CAS: 1447811-16-6
• 化学式: C₄₀H₅₀F₃NO₉Si
• 分子量: 773.919
• InChiKey: VYEDBYIIIJRTNQ-IRJXWVIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.64
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-O-(2-benzyloxyethyl)-2-deoxy-3,4-di-O-benzoyl-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 20% palladium hydroxide-activated charcoal 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 154.0h， 生成 4-(((2R,3S,4R,5R,6R)-3,4-bis(benzoyloxy)-6-(2-(bis(4-methoxyphenyl)(phenyl)methoxy)ethoxy)-5-(2,2,2-trifluoroacetamido)tetrahydro-2H-pyran-2-yl)methoxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis of oligonucleotides with glucosamine at the 3′-position and evaluation of their biological activity

  摘要：

  Short interfering RNA (siRNA) has been proven to be an utilizable tool for post-transcriptional gene silencing research. In this study, we designed and synthesized two glucosamine analogues and tried to modify the siRNA using these two glucosamine analogues at the 3'-overhang region of siRNAs to improve the nuclease resistance and to overcome some other weak points. The siRNAs modified with glucosamine analogues had almost no effect of the thermal stability and showed strong resistance to nuclease degradation. Some of them kept the same gene silencing activity level as unmodified siRNA. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.036
• 作为产物：
  描述：

  phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 1-O-(2-benzyloxyethyl)-2-deoxy-3,4-di-O-benzoyl-2-trifluoroacetylamino-6-O-triisopropylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of oligonucleotides with glucosamine at the 3′-position and evaluation of their biological activity

  摘要：

  Short interfering RNA (siRNA) has been proven to be an utilizable tool for post-transcriptional gene silencing research. In this study, we designed and synthesized two glucosamine analogues and tried to modify the siRNA using these two glucosamine analogues at the 3'-overhang region of siRNAs to improve the nuclease resistance and to overcome some other weak points. The siRNAs modified with glucosamine analogues had almost no effect of the thermal stability and showed strong resistance to nuclease degradation. Some of them kept the same gene silencing activity level as unmodified siRNA. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.036

文献信息

• Synthesis of oligonucleotides with glucosamine at the 3′-position and evaluation of their biological activity
  作者：Xiong Luo、Takahiro Sugiura、Remi Nakashima、Yoshiaki Kitamura、Yukio Kitade

  DOI：10.1016/j.bmcl.2013.05.036

  日期：2013.7

  Short interfering RNA (siRNA) has been proven to be an utilizable tool for post-transcriptional gene silencing research. In this study, we designed and synthesized two glucosamine analogues and tried to modify the siRNA using these two glucosamine analogues at the 3'-overhang region of siRNAs to improve the nuclease resistance and to overcome some other weak points. The siRNAs modified with glucosamine analogues had almost no effect of the thermal stability and showed strong resistance to nuclease degradation. Some of them kept the same gene silencing activity level as unmodified siRNA. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.