p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside | 220645-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(4-methylphenyl)sulfanyl-5-(4-oxopentanoyloxy)-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-yl] benzoate
• CAS: 220645-28-3
• 化学式: C₇₅H₈₀O₁₃SSi
• 分子量: 1249.6
• InChiKey: PCYNTBWETJQLST-CURPXMHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.98
• 重原子数：
  90
• 可旋转键数：
  31
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside 在 氟化氢吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 以79%的产率得到p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-4-O-levulinyl-1-thio-β-D-galactopyranoside
  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：

  p-methylphenyl 6-O-tert-butyldiphenylsilyl-4-O-levulinyl-3-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.66h， 生成 p-methylphenyl 2-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-4-O-levulinyl-1-thio-β-D-galactopyranoside
  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
  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.