ethyl 2,6-di-O-benzoyl-β-D-galactopyranoside | 164112-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,6-di-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-5-benzoyloxy-6-ethoxy-3,4-dihydroxyoxan-2-yl]methyl benzoate
• CAS: 164112-41-8
• 化学式: C₂₂H₂₄O₈
• 分子量: 416.428
• InChiKey: BZUDSKIUCVWGDT-GPUAKUCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2,6-di-O-benzoyl-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成
  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：

  beta-D-半乳糖五乙酸酯 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 氢溴酸 、 sodium methylate 、 乙酸酐 、 对甲苯磺酸 、 溶剂黄146 、 silver carbonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 100.0h， 生成 ethyl 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

文献信息

• One-Pot Synthesis of Lewis X Oligosaccharide Derivatives Using "Armed-Disarmed" Coupling Method
  作者：Masahiro Yoshida、Takao Kiyoi、Takahiro Tsukida、Hirosato Kondo

  DOI：10.1080/07328309808002344

  日期：1998.5.1

  Abstract A stereocontrolled synthesis of Lex oligosaccharide derivatives using a facile one-pot, two-step glycosylation based on the “Armed-Disarmed” concept are described. The first coupling of phenyl O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galacto-pyranosyl)-(1→4)-2,6-di-O-benzoyl-1-thio-β-D-glucopyranoside (2) with phenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (3) using N-iodosuccinimide (N

  摘要描述了一种基于“武装解除”概念的简便的一锅两步糖基化立体控制合成Lex寡糖衍生物的方法。苯基O-（2,6-二-O-苯甲酰基-3,4-O-异亚丙基-β-D-半乳糖-吡喃糖基）-（1→4）-2,6-二-O-苯甲酰基的首次偶联使用N-碘代琥珀酰亚胺（NIS）-三氟甲磺酸（-1）将-1-硫代-β-D-吡喃葡萄糖苷（2）与苯基2,3,4-三-O-苄基-1-硫代-β-L-呋喃果糖苷（3）（ （TfOH）得到三糖（8），将其未经纯化而进行第二次缩合，用一些受体如2,4,6-三-O-苄基-β-D-D-吡喃半乳糖苷（4），2,6-二乙基乙基-O-苯甲酰基-β-D-吡喃半乳糖苷（5），乙基O-（2,6-二-O-苄基-β-D-吡喃半乳糖基）-（1→4）-2,3,6-tri-O -苄基-β-D-吡喃葡萄糖苷（6）和乙基O-（2,6-二-O-苯甲酰基-β-D-吡喃半乳糖基）-（1→4）-2,3，6-三-O-苄基
• Solution- and Solid-Phase Synthesis of Inhibitors of H. pylori Attachment and E-Selectin-Mediated Leukocyte Adhesion
  作者：Randall L. Halcomb、Hongmei Huang、Chi-Huey Wong

  DOI：10.1021/ja00104a011

  日期：1994.12

  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.