(4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one | 183954-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one
• 英文别名: (4aS,5R,7S,8R,8aS)-8-phenylmethoxy-5-(phenylmethoxymethyl)-7-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-3-one
• CAS: 183954-70-3
• 化学式: C₅₆H₅₈O₁₂
• 分子量: 923.069
• InChiKey: WYSFSGSZOGBVRQ-AGBKSPKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  68
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one 在 palladium dihydroxide sodium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.17h， 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：

  3,4-isopropylidene-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 在 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 、 溶剂黄146 作用下， 反应 24.0h， 生成 (4aS,5R,7S,8R,8aS)-8-Benzyloxy-5-benzyloxymethyl-7-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,4-b][1,4]dioxin-3-one
  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.