5-methoxycarbonylpentyl 2-deoxy-2-phthalimido-β-D-glucopyranoside | 220645-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxycarbonylpentyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: 5-Methoxycarbonylpentyl 2-Deoxy-2-phthalimido-beta-D-glucopyranoside；methyl 6-[(2R,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoate
• CAS: 220645-76-1
• 化学式: C₂₁H₂₇NO₉
• 分子量: 437.447
• InChiKey: DLXDWLHZVQTHQE-GANPKANLSA-N

物化性质

• 沸点：
  626.9±55.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylpentyl 2-deoxy-2-phthalimido-β-D-glucopyranoside 在 D(+)-10-樟脑磺酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 5.17h， 生成 5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Programmable One-Pot Oligosaccharide Synthesis

  摘要：

  In an effort to develop a broadly applicable approach to the facile one-pot synthesis of oligosaccharides, the reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We have characterized and quantified the influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor. In addition, we have established a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by H-1 NMR. Using the reactivity data, we have created a database of thioglycosides as glycosyl donors and demonstrated its utility in the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures. In addition, we have developed the first computer program, OptiMer, for use as a database search tool and guide for the selection of building blocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.

  DOI：

  10.1021/ja982232s
• 作为产物：
  描述：

  6-羟基己酸甲酯 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-methoxycarbonylpentyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Programmable One-Pot Oligosaccharide Synthesis

  摘要：

  In an effort to develop a broadly applicable approach to the facile one-pot synthesis of oligosaccharides, the reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We have characterized and quantified the influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor. In addition, we have established a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by H-1 NMR. Using the reactivity data, we have created a database of thioglycosides as glycosyl donors and demonstrated its utility in the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures. In addition, we have developed the first computer program, OptiMer, for use as a database search tool and guide for the selection of building blocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.

  DOI：

  10.1021/ja982232s

文献信息

• Programmable one-pot oligosaccharide synthesis
  申请人：The Scripps Research Institute

  公开号：US20040024201A1

  公开（公告）日：2004-02-05

  The reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC in conjunction with the development of a broadly applicable approach for a facile one-pot synthesis of oligosaccharides. The influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor is characterized and quantified. In addition, a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by 1 H NMR has been established. A database of thioglycosides as glycosyl donors has been created using this reactivity data. The utility is demonstrated by the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures. In addition, a computer program as been described for use as a database search tool and guide for the selection of building blocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.

  一些全保护或有一个羟基暴露的对甲苯硫代糖苷(STol)供体的反应性已经通过HPLC定量测定，并结合开发了一种广泛适用的易于一锅法合成寡糖的方法进行了研究。不同单糖核心和不同保护基对每个糖苷供体的结构影响和反应性进行了表征和量化。此外，已经建立了糖基供体反应性和1 H NMR的异构质子化学位移之间的相关性。使用这种反应性数据创建了硫代糖苷作为糖基供体的数据库。通过易于快速的一锅组装各种线性和分支寡糖结构来展示其实用性。此外，还描述了一种计算机程序，用作数据库搜索工具和选择构建块以一锅法组装所需寡糖或单个寡糖库的指南。
• US6538117B1
  申请人：——

  公开号：US6538117B1

  公开（公告）日：2003-03-25
• Programmable One-Pot Oligosaccharide Synthesis
  作者：Zhiyuan Zhang、Ian R. Ollmann、Xin-Shan Ye、Ralf Wischnat、Timor Baasov、Chi-Huey Wong

  DOI：10.1021/ja982232s

  日期：1999.2.1

  In an effort to develop a broadly applicable approach to the facile one-pot synthesis of oligosaccharides, the reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We have characterized and quantified the influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor. In addition, we have established a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by H-1 NMR. Using the reactivity data, we have created a database of thioglycosides as glycosyl donors and demonstrated its utility in the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures. In addition, we have developed the first computer program, OptiMer, for use as a database search tool and guide for the selection of building blocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.