2,6-di-O-benzyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside | 183954-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-di-O-benzyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane-3,4-diol
• CAS: 183954-69-0
• 化学式: C₅₄H₅₈O₁₁
• 分子量: 883.048
• InChiKey: WJSHHYRSSOSLFO-NFQHRERGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  65
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,6-di-O-benzyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 在 palladium dihydroxide sodium hydroxide 、 氢气 、 四丁基碘化铵 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 6.17h， 生成 [(2R,3S,4S,5R,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-acetic acid
  参考文献：
  名称：

  Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin

  摘要：

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.

  DOI：

  10.1021/ja9611093
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 在 甲醇 、 camphor-10-sulfonic acid 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 24.5h， 生成 2,6-di-O-benzyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin

  摘要：

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.

  DOI：

  10.1021/ja9611093

文献信息

• Rational Design and Synthesis of a 1,1-Linked Disaccharide That Is 5 Times as Active as Sialyl Lewis X in Binding to E-Selectin
  作者：Kazumi Hiruma、Tetsuya Kajimoto、Gabriel Weitz-Schmidt、Ian Ollmann、Chi-Huey Wong

  DOI：10.1021/ja9611093

  日期：1996.1.1

  We describe here a rational design and synthesis of (3-O-carboxymethyl)-beta-D-galactopyranosyl alpha-D-mannopyranoside which is 5 times as active as sialyl Lewis X in binding to E-selectin and also effective against P- and L-selectin. A new method for the 1,1-glycosidic bond formation via coupling of protected trimethylsilyl beta-D-galactoside and alpha-mannosyl fluoride in the presence of BF3 . Et(2)O is described.