[3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranosyl azide | 252845-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranosyl azide
• CAS: 252845-49-1
• 化学式: C₂₀H₂₉N₃O₁₁
• 分子量: 487.464
• InChiKey: GKHRPGGGRQQNIH-KBAZAOLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.85
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  216.29
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranosyl azide 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 6.0h， 以92%的产率得到[3-O-(4-methoxybenzyl) 2,4,6-tri-O-acetyl-β-D-galactopyranosyl]-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Large Scale Synthesis of A Derivative of An α-Galactosyl Trisaccharide Epitope Involved in the Hyperacute Rejection of Xenotransplantation

  摘要：

  A derivative of an alpha-galactosyl trisaccharide xenoactive antigen, (2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1-->3)-(2,4,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide (5), was synthesized on a large scale (50 gram). The synthesis involved a high yielding and highly stereoselective (alpha \beta>20:1) glycosylation reaction utilizing a thiogalactoside as the donor and a selectively protected lactose azide as the acceptor. This derivative serves as a versatile intermediate that can be transformed into a variety of alpha-Gal containing glycoconjugates highly desired in xenotransplantation research and pharmaceutical development.

  DOI：

  10.1080/07328309908544050
• 作为产物：
  描述：

  lactosyl azide 在 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 [3-O-(4-methoxybenzyl)-β-D-galactopyranosyl]-(1->4)-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Large Scale Synthesis of A Derivative of An α-Galactosyl Trisaccharide Epitope Involved in the Hyperacute Rejection of Xenotransplantation

  摘要：

  A derivative of an alpha-galactosyl trisaccharide xenoactive antigen, (2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-(1-->3)-(2,4,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide (5), was synthesized on a large scale (50 gram). The synthesis involved a high yielding and highly stereoselective (alpha \beta>20:1) glycosylation reaction utilizing a thiogalactoside as the donor and a selectively protected lactose azide as the acceptor. This derivative serves as a versatile intermediate that can be transformed into a variety of alpha-Gal containing glycoconjugates highly desired in xenotransplantation research and pharmaceutical development.

  DOI：

  10.1080/07328309908544050