5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-phthalimido-β-D-glucopyranoside | 220645-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-phthalimido-β-D-glucopyranoside
• 英文别名: methyl 6-[[(4aR,6R,7R,8R,8aS)-7-(1,3-dioxoisoindol-2-yl)-2-(4-methoxyphenyl)-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]hexanoate
• CAS: 220645-89-6
• 化学式: C₃₆H₃₉NO₁₀
• 分子量: 645.706
• InChiKey: XDLMOXNMRQXWDJ-ITLRBVJTSA-N

物化性质

• 沸点：
  746.6±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-4,6-O-p-methoxybenzylidene-2-phthalimido-β-D-glucopyranoside 在 3 A molecular sieve 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到5-methoxycarbonylpentyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-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 、 D(+)-10-樟脑磺酸 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 11.17h， 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

文献信息

• 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.