2'-(benzyloxycarbonyl)benzyl (2-O-benzoyl-4-O-benzyl-3-O-p-methoxybenzyl-α-D-rhamnopyranosyl)-(1->2)-(4,6-di-O-benzyl-3-C-methyl-α-D-manno-hexopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside | 1001082-43-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(benzyloxycarbonyl)benzyl (2-O-benzoyl-4-O-benzyl-3-O-p-methoxybenzyl-α-D-rhamnopyranosyl)-(1->2)-(4,6-di-O-benzyl-3-C-methyl-α-D-manno-hexopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
• 英文别名: benzyl 2-[[(2R,3R,4R,5S,6S)-3-benzoyloxy-4-[(2R,3S,4S,5R,6R)-3-[(2R,3S,4S,5R,6R)-3-benzoyloxy-4-[(4-methoxyphenyl)methoxy]-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-4-hydroxy-4-methyl-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-methyl-5-phenylmethoxyoxan-2-yl]oxymethyl]benzoate
• CAS: 1001082-43-4
• 化学式: C₈₄H₈₆O₁₉
• 分子量: 1399.6
• InChiKey: OSUNQLPFFHSBGY-QLFPAPIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.8
• 重原子数：
  103
• 可旋转键数：
  34
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  210
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2'-(benzyloxycarbonyl)benzyl (2-O-benzoyl-4-O-benzyl-3-O-p-methoxybenzyl-α-D-rhamnopyranosyl)-(1->2)-(4,6-di-O-benzyl-3-C-methyl-α-D-manno-hexopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 在 palladium on activated charcoal 乙酸铵 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以92%的产率得到2'-carboxybenzyl (2-O-benzoyl-4-O-benzyl-3-O-p-methoxybenzyl-α-D-rhamnopyranosyl)-(1->2)-(4,6-di-O-benzyl-3-C-methyl-α-D-manno-hexopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Tri-, Hexa-, and Nonasaccharide Subunits of the Atypical O-Antigen Polysaccharide of the Lipopolysaccharide from Danish Helicobacter pylori Strains

  摘要：

  Synthesis of trisaccharide repeating unit, -> 3)-alpha-D-Rhap-(1 -> 2)-alpha-D-Manp3CMe-(1 -> 3)-alpha-L-Rha p-(1 ->, and its dimeric hexa- and trimeric nonasaccharide subunits of the atypical O-antigen polysaccharide of the lipopolysaccharide from Danish H. pylori strains D1, D3, and D6 has been accomplished. Successful synthesis of the hexasaccharide and the nonasaccharide was possible by dimerization and trimerization of the suitably protected trisaccharide repeating unit, in which three monosaccharide moieties were arranged in a proper order by placing the sterically demanding 3-C-methyl-D-mannose moiety in between D- and L-rhamnoses. Key steps include the coupling of three monosaccharide moieties and dimerization and trimerization of the trisaccharide unit by glycosylations employing the 2'-carboxybenzyl glycoside method.. Also presented is a method for the synthesis of the novel branched sugar, 3-C-methyl-D-mannose moiety by elaboration of its equatorial hydroxyl and axial methyl groups at C-3' in the disaccharide stage.

  DOI：

  10.1021/jo701531x
• 作为产物：
  描述：

  2'-carboxybenzyl 2-O-benzoyl-4-O-benzyl-3-O-p-methoxybenzyl-α-D-rhamnopyranoside 、 2'-(benzyloxycarbonyl)benzyl (4,6-di-O-benzyl-3-C-methyl-α-D-manno-hexopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以75%的产率得到2'-(benzyloxycarbonyl)benzyl (2-O-benzoyl-4-O-benzyl-3-O-p-methoxybenzyl-α-D-rhamnopyranosyl)-(1->2)-(4,6-di-O-benzyl-3-C-methyl-α-D-manno-hexopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Tri-, Hexa-, and Nonasaccharide Subunits of the Atypical O-Antigen Polysaccharide of the Lipopolysaccharide from Danish Helicobacter pylori Strains

  摘要：

  Synthesis of trisaccharide repeating unit, -> 3)-alpha-D-Rhap-(1 -> 2)-alpha-D-Manp3CMe-(1 -> 3)-alpha-L-Rha p-(1 ->, and its dimeric hexa- and trimeric nonasaccharide subunits of the atypical O-antigen polysaccharide of the lipopolysaccharide from Danish H. pylori strains D1, D3, and D6 has been accomplished. Successful synthesis of the hexasaccharide and the nonasaccharide was possible by dimerization and trimerization of the suitably protected trisaccharide repeating unit, in which three monosaccharide moieties were arranged in a proper order by placing the sterically demanding 3-C-methyl-D-mannose moiety in between D- and L-rhamnoses. Key steps include the coupling of three monosaccharide moieties and dimerization and trimerization of the trisaccharide unit by glycosylations employing the 2'-carboxybenzyl glycoside method.. Also presented is a method for the synthesis of the novel branched sugar, 3-C-methyl-D-mannose moiety by elaboration of its equatorial hydroxyl and axial methyl groups at C-3' in the disaccharide stage.

  DOI：

  10.1021/jo701531x

文献信息

• Synthesis of Tri-, Hexa-, and Nonasaccharide Subunits of the Atypical O-Antigen Polysaccharide of the Lipopolysaccharide from Danish <i>Helicobacter </i><i>pylori</i> Strains
  作者：Dinanath Baburao Fulse、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1021/jo701531x

  日期：2007.12.1

  Synthesis of trisaccharide repeating unit, -> 3)-alpha-D-Rhap-(1 -> 2)-alpha-D-Manp3CMe-(1 -> 3)-alpha-L-Rha p-(1 ->, and its dimeric hexa- and trimeric nonasaccharide subunits of the atypical O-antigen polysaccharide of the lipopolysaccharide from Danish H. pylori strains D1, D3, and D6 has been accomplished. Successful synthesis of the hexasaccharide and the nonasaccharide was possible by dimerization and trimerization of the suitably protected trisaccharide repeating unit, in which three monosaccharide moieties were arranged in a proper order by placing the sterically demanding 3-C-methyl-D-mannose moiety in between D- and L-rhamnoses. Key steps include the coupling of three monosaccharide moieties and dimerization and trimerization of the trisaccharide unit by glycosylations employing the 2'-carboxybenzyl glycoside method.. Also presented is a method for the synthesis of the novel branched sugar, 3-C-methyl-D-mannose moiety by elaboration of its equatorial hydroxyl and axial methyl groups at C-3' in the disaccharide stage.