p-nitrophenyl 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-β-D-galactopyranoside | 76328-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-β-D-galactopyranoside
• 英文别名: 4-nitrophenyl O-(β-D-galactopyranosyl)-(1-3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-β-D-galactopyranoside；Gal(b1-3)GlcNAc(b1-3)Gal(b)-O-Ph(4-NO2)；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-4-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 76328-92-2
• 化学式: C₂₆H₃₈N₂O₁₈
• 分子量: 666.59
• InChiKey: HUTJAMJEIUSQKQ-PWQPIJDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  312
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-α-D-galactopyranosyl bromide 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 20.0h， 生成 p-nitrophenyl 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-glucopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  合成粘蛋白片段：3-O- [2-乙酰氨基-4,6-二-O-乙酰基-2-脱氧-3-O-（2,3,4,6-四-O-乙酰基-bD-吡喃半乳糖基） -bD-吡喃葡萄糖基] -2,4,6-三-O-乙酰基-aD-吡喃半乳糖基溴化物和对硝基苯基3-O-（2-乙酰氨基-2-脱氧-3-ObD-吡喃吡喃糖基-bD吡喃葡萄糖基）-bD -半乳糖吡喃糖苷。

  摘要：

  DOI：

  10.1016/0008-6215(84)85234-9

文献信息

• A convenient synthesis of lacto-N-biose I [β-d-Galp-(1 → 3)-β-d-GlcpNAc] linked oligosaccharides from phenyl O-(tetra-O-acetyl-β-d-galactopyranosyl)-(1 → 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside
  作者：Rakesh K. Jain、Robert D. Locke、Khushi L. Matta

  DOI：10.1016/0008-6215(93)80103-l

  日期：1993.3

  The synthesis of two tetrasaccharides and one trisaccharide containing lacto-N-biose I (β-d-Galp-(1 → 3)-β-d-GlcpNAc) as their terminal unit was accomplished through development and utilization of a key glycosyl donor, namely, phenyl O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1 → 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-d-glucopyranoside.

  通过开发和利用关键的糖基供体，完成了以乳酸-N-二糖I（β-d-Galp-（1→3）-β-d-GlcpNAc）为末端单元的两种四糖和一种三糖的合成，即苯基O-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-（1→3）-4,6-二-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-1-硫代-β-d-吡喃葡萄糖苷。
• Synthetic mucin fragments: 3-O-[2-Acetamido-4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-β-d- glucopyranosyl]-2,4,6-tri-O-acetyl-α-d-galactopyranosyl bromide and p-nitrophenyl 3-O-(2-acetamido-2-deoxy-3-O-β-d-galactopyranosyl-β-d-glucopyranosyl)-β-d-galactopyranoside
  作者：Katsunori Kohata、Saeed A. Abbas、Khushi L. Matta

  DOI：10.1016/0008-6215(84)85234-9

  日期：1984.9