methyl 2,3,4-tri-O-benzoyl-6-O--β-D-galactopyranoside | 170298-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-O--β-D-galactopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzoyl-6-O-(methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-α-D-neuraminate-2-yl)-β-D-galactopyranoside；methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]-2-[[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-methoxyoxan-2-yl]methoxy]oxane-2-carboxylate
• CAS: 170298-69-8
• 化学式: C₄₈H₅₃NO₂₁
• 分子量: 979.943
• InChiKey: YHTFZBXZTPQXER-IEHMQUOASA-N

物化性质

• 沸点：
  958.5±65.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  70
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  276
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O--β-D-galactopyranoside 在 sodium methylate 、 sodium hydroxide 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 以55%的产率得到methyl [(3,5-dideoxy-5-acetamido-D-glycero-α-D-gulo-non-2-ulopyranosid)onic acid](2→3)β-D-galactopyranoside
  参考文献：
  名称：

  Design and synthesis of a multivalent homing device for targeting to murine CD22

  摘要：

  CD22 is a cell-surface glycoprotein uniquely located on mature B-cells and B-cell derived tumour cells. Current evidence suggests that binding of endogenous ligands to CD22 leads to modulation of B-cell activation by antigen. Incidentally, however, B-cell activation may derail, and lead to an undesired immune response, for example in cases of allergy, rheumatoid arthritis and Crohn's disease. In this situation, synthetic high-affinity ligands for CD22 may be of therapeutic value as inhibitors of B-cell activation. Recent studies have revealed that natural ligands for CD22 contain the trisaccharide NeuAc alpha -2,6-Lac as the basic binding motif. In addition, it has been demonstrated that binding to CD22 is strongly enhanced by multivalent presentation of the basic binding motif (cluster effect). In this paper, the stepwise development of a novel multivalent high-affinity ligand for CD22 is described. In the first stage, a series of monovalent NeuAc alpha -2,6-Glc(Y)X type binding motifs was prepared, and their affinity for murine CD22 was monitored, to obtain more insight into the effect of separate structure elements on ligand recognition. In the second stage, we prepared a trivalent cluster, based on the monovalent motif that displayed the highest affinity for CD22, NeuAccc2,6-GlcNBzNO(2)OMe (7). This cluster, TRIS(NeuAc alpha -2,6-GlcNBzNO(2))(3) (52), displayed a more than 58-fold higher affinity for CD22 than the reference structure NeuAc alpha -2,6-LacOMe (10). To our knowledge, the cluster 52 is one of the most potent antagonists for CD22, yet synthesised. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00224-8
• 作为产物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranosate 在 吡啶 、 silver perchlorate 、 二氯二甲基硅烷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 8.0h， 生成 methyl 2,3,4-tri-O-benzoyl-6-O--β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis ofN-Acetyl-α-neuraminosyl-galactose Disaccharide

  摘要：

  由二氯二甲基硅烷和高氯酸银生成的催化剂有效地促进了丙腈中具有容易获得的乙酰氧基或苯氧羰基氧基离去基团的 N-乙酰神经氨酸（Neu5Ac）供体与 d-半乳糖的 6-OH 位异构体的糖基化，从而以良好的收率和立体选择性得到相应的 α-半乳糖苷。

  DOI：

  10.1246/cl.1995.455