2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside | 184178-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 184178-66-3
• 化学式: C₄₈H₅₄O₁₅
• 分子量: 870.948
• InChiKey: ITVRWGCDYDXSQA-FMNSLDAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  63
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  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 、 四丁基碘化铵 、 sodium hydride 、 二正丁基氧化锡 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 26.5h， 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
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-D-半乳糖 、 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride 在 silver perchlorate 、 tin(ll) chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 以27%的产率得到2,3,4,6-tetra-O-acetyl-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