2-[(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxy]pyridine | 28708-23-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxy]pyridine
• 英文别名: 2-(Tetra-O-benzoyl-1-β-D-glucopyranosyloxy)-pyridin
• CAS: 28708-23-8
• 化学式: C₃₉H₃₁NO₁₀
• 分子量: 673.676
• InChiKey: VYSUZJYLSBCTTG-ZGJPNWFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  136.55
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 2-[(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxy]pyridine 在 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以92%的产率得到methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol

  摘要：

  2-Pyridyl glycosides have been identified to be powerful glycosyl donors for the preactivation-based oligosaccharide synthesis. By using stoichiometric amount of Tf2O, the 2-pyridyl glycosides were pre-activated, which subsequently underwent glycosylation reactions smoothly to produce the coupled products in high yields. Furthermore, the 2-pyridyl glycosides were applied to the efficient oligosaccharide assembly by the preactivation-based one-pot oligosaccharide synthesis protocol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.066
• 作为产物：
  描述：

  2-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyloxy)-pyridin 在 吡啶 、 甲醇 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 2-[(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)oxy]pyridine
  参考文献：
  名称：

  2-Pyridyl glycoside: an alternative glycosyl donor in preactivation protocol

  摘要：

  2-Pyridyl glycosides have been identified to be powerful glycosyl donors for the preactivation-based oligosaccharide synthesis. By using stoichiometric amount of Tf2O, the 2-pyridyl glycosides were pre-activated, which subsequently underwent glycosylation reactions smoothly to produce the coupled products in high yields. Furthermore, the 2-pyridyl glycosides were applied to the efficient oligosaccharide assembly by the preactivation-based one-pot oligosaccharide synthesis protocol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.066

文献信息

• Effective synthesis of nucleosides with glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.tetlet.2008.06.042

  日期：2008.8

  Glycosyl trifluoroacetimidates have been disclosed to be effective glycosyl donors for the synthesis of nucleosides; the present N-glycosylation protocol requires only a catalytic amount of TMSOTf as promoter and proceeds smoothly at room temperature. (c) 2008 Elsevier Ltd. All rights reserved.