benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside | 493019-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
• CAS: 493019-68-4
• 化学式: C₅₅H₅₃NO₁₂
• 分子量: 920.025
• InChiKey: ZQXKCPFCICSVHS-NVIPDBDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  68.0
• 可旋转键数：
  17.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  140.68
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  苯基2,3,4,6-四-O-苯甲基-1-硫代-Β-D-半乳糖皮蒽 、 benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 在 4 A molecular sieve 、 DMTST 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and inhibitory activity of a di- and a trisaccharide corresponding to an erythrocyte glycolipid responsible for the nor polyagglutination

  摘要：

  The polyagglutinable erythrocytes NOR contain unusual neutral glycolipids reactive with anti-NOR antibodies. The disaccharide alpha-D-Galp-(1-->4)-D-GalpNAc and the trisaccharide alpha-D-Galp-(1-->4)-beta-D-GalpNAc-(1-->3)-D-Gal corresponding to the non-reducing end of a NOR glycolipid (NOR1) were chemically synthesized. The syntheses were based on a common (1-->4)-beta-D-GalNAc precursor, and utilized benzyl glycoside and benzyl ether functions for persistent blocking of hydroxyls. The alpha-D-Galp-(1-->4)-beta-D-GalpNAc structural element has been found only recently in Nature, and derivatives thereof have not been synthesized before. Both the synthesized oligosaccharides inhibited specifically human anti-NOR antibodies, the trisaccharide being 300 times more active than the disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00222-7
• 作为产物：
  描述：

  ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 4 A molecular sieve 、 sodium methylate 、 DMTST 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 benzyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and inhibitory activity of a di- and a trisaccharide corresponding to an erythrocyte glycolipid responsible for the nor polyagglutination

  摘要：

  The polyagglutinable erythrocytes NOR contain unusual neutral glycolipids reactive with anti-NOR antibodies. The disaccharide alpha-D-Galp-(1-->4)-D-GalpNAc and the trisaccharide alpha-D-Galp-(1-->4)-beta-D-GalpNAc-(1-->3)-D-Gal corresponding to the non-reducing end of a NOR glycolipid (NOR1) were chemically synthesized. The syntheses were based on a common (1-->4)-beta-D-GalNAc precursor, and utilized benzyl glycoside and benzyl ether functions for persistent blocking of hydroxyls. The alpha-D-Galp-(1-->4)-beta-D-GalpNAc structural element has been found only recently in Nature, and derivatives thereof have not been synthesized before. Both the synthesized oligosaccharides inhibited specifically human anti-NOR antibodies, the trisaccharide being 300 times more active than the disaccharide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00222-7