ethyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)(1<*>3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside | 164112-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)(1<*>3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3-acetyloxy-5-benzoyloxy-4-[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxy-6-ethoxyoxan-2-yl]methyl benzoate
• CAS: 164112-43-0
• 化学式: C₄₄H₄₅NO₁₈
• 分子量: 875.837
• InChiKey: BRSUJRFVWWYRBO-LHGRFTGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  232
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  ethyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)(1<*>3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside 在 sodium methylate 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 ethyl 3-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion

  摘要：

  Chemical and enzymatic methods have been developed for the synthesis of the oligosaccharides NeuAc alpha 2-->3Gal beta 1 -->4GlcNAc beta 1-->3Gal and NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->3Gal as inhibitors for H. pylori and E-selectin, respectively. Gal, NeuAc, and Fuc were incorporated sequentially into the synthetic primer GlcNAc beta 1-->3Gal beta OEt by the corresponding glycosyltransferases to give both the tetrasaccharide and the pentasaccharide. This solution-phase strategy was then extended to the solid-phase synthesis of the tetrasaccharide. A disaccharide primer was first attached to controlled pore glass via a spacer group containing an ester bond, followed by enzymatic incorporation of Gal and NeuAc. Two to three equivalents of sugar nucleotides were used in the enzymatic glycosylationl and the conversion for each step was found to be > 98% as indicated in the analysis of products released by treatment with hydrazine.

  DOI：

  10.1021/ja00104a011
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 93.0h， 生成 ethyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)(1<*>3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion

  摘要：

  Chemical and enzymatic methods have been developed for the synthesis of the oligosaccharides NeuAc alpha 2-->3Gal beta 1 -->4GlcNAc beta 1-->3Gal and NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->3Gal as inhibitors for H. pylori and E-selectin, respectively. Gal, NeuAc, and Fuc were incorporated sequentially into the synthetic primer GlcNAc beta 1-->3Gal beta OEt by the corresponding glycosyltransferases to give both the tetrasaccharide and the pentasaccharide. This solution-phase strategy was then extended to the solid-phase synthesis of the tetrasaccharide. A disaccharide primer was first attached to controlled pore glass via a spacer group containing an ester bond, followed by enzymatic incorporation of Gal and NeuAc. Two to three equivalents of sugar nucleotides were used in the enzymatic glycosylationl and the conversion for each step was found to be > 98% as indicated in the analysis of products released by treatment with hydrazine.

  DOI：

  10.1021/ja00104a011