2-naphthylmethyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside | 316810-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-naphthylmethyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• 英文别名: (4aR,6S,7R,8R,8aR)-7-azido-6-(naphthalen-2-ylmethoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 316810-22-7
• 化学式: C₂₄H₂₃N₃O₅
• 分子量: 433.464
• InChiKey: UXYMZEDFAJWVAJ-SCUNIMLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-naphthylmethyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 2-naphthylmethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->3)-2-azido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and glycan priming activity of acetylated disaccharides

  摘要：

  Five disaccharides related in structure to the glycans of vertebrate mucins have been chemically synthesized using orthogonal blocking, coupling and deblocking techniques. These include 2-naphthylmethyl 3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-beta -D-glucopyranoside (6), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O -acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O -acetyl-beta -D-galactopyranoside (14), 2-naphthylmethy12,3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside oside (20), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2-acetamido-4, 6-di-O -acetyl-2-deoxy-or-D-galactopyranoside (23) and 2-naphthylmethyl 2-acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside (27). These per-O-acetylated compounds were fed to U-937 cells to test their ability to prime oligosaccharide synthesis, inhibit glycoprotein biosynthesis and alter adhesion to E-selectin expressed on endothelial cells. The results show that 6, 14, and 20 served as substrates for oligosaccharide synthesis. The generation of glycoside-primed glycans altered the formation of glycoproteins on the cell surface and inhibited cell adhesion dependent on E-selectin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00200-7
• 作为产物：
  描述：

  2-naphthylmethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-naphthylmethyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis and glycan priming activity of acetylated disaccharides

  摘要：

  Five disaccharides related in structure to the glycans of vertebrate mucins have been chemically synthesized using orthogonal blocking, coupling and deblocking techniques. These include 2-naphthylmethyl 3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-beta -D-glucopyranoside (6), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O -acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O -acetyl-beta -D-galactopyranoside (14), 2-naphthylmethy12,3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside oside (20), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2-acetamido-4, 6-di-O -acetyl-2-deoxy-or-D-galactopyranoside (23) and 2-naphthylmethyl 2-acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside (27). These per-O-acetylated compounds were fed to U-937 cells to test their ability to prime oligosaccharide synthesis, inhibit glycoprotein biosynthesis and alter adhesion to E-selectin expressed on endothelial cells. The results show that 6, 14, and 20 served as substrates for oligosaccharide synthesis. The generation of glycoside-primed glycans altered the formation of glycoproteins on the cell surface and inhibited cell adhesion dependent on E-selectin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00200-7

文献信息

• Synthesis and glycan priming activity of acetylated disaccharides
  作者：Arun K Sarkar、Jillian R Brown、Jeffrey D Esko

  DOI：10.1016/s0008-6215(00)00200-7

  日期：2000.11

  Five disaccharides related in structure to the glycans of vertebrate mucins have been chemically synthesized using orthogonal blocking, coupling and deblocking techniques. These include 2-naphthylmethyl 3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-beta -D-glucopyranoside (6), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O -acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O -acetyl-beta -D-galactopyranoside (14), 2-naphthylmethy12,3,4,6-tetra-O-acetyl-beta -D-galactopyranosyl-(1 --> 3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside oside (20), 2-naphthylmethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 3)-2-acetamido-4, 6-di-O -acetyl-2-deoxy-or-D-galactopyranoside (23) and 2-naphthylmethyl 2-acetamido-3,4, 6-tri-O-acetyl-2-deoxy-beta -D-glucopyranosyl-(1 --> 6)-2-acetamido-3,4-di-O-acetyl-2-deoxy-alpha -D-galactopyranoside (27). These per-O-acetylated compounds were fed to U-937 cells to test their ability to prime oligosaccharide synthesis, inhibit glycoprotein biosynthesis and alter adhesion to E-selectin expressed on endothelial cells. The results show that 6, 14, and 20 served as substrates for oligosaccharide synthesis. The generation of glycoside-primed glycans altered the formation of glycoproteins on the cell surface and inhibited cell adhesion dependent on E-selectin. (C) 2000 Elsevier Science Ltd. All rights reserved.