1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-3,4,6-tri-O-acetyl-β-D-glucopyranoside | 1261030-95-8

• 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-2-phthalimino-3,4,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: 2-benzyloxyethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-(2-phenylmethoxyethoxy)oxan-2-yl]methyl acetate
• CAS: 1261030-95-8
• 化学式: C₂₉H₃₁NO₁₁
• 分子量: 569.565
• InChiKey: GLFGRMXIBFUNNV-ZOLYYXPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-3,4,6-tri-O-acetyl-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 氢气 、 palladium(II) hydroxide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 89.0h， 生成 2-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyloxy)ethyl(2-cyanoethyl)(N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y
• 作为产物：
  描述：

  D-氨基葡萄糖盐酸盐 在 吡啶 、 三氟化硼-二甲醚络合物 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 26.0h， 生成 1-O-(2-benzyloxyethyl)-2-deoxy-2-phthalimino-3,4,6-tri-O-acetyl-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