3-azidopropyl (methyl (2,3-di-O-benzoyl-β-D-glucopyranosid) uronate) | 946390-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl (methyl (2,3-di-O-benzoyl-β-D-glucopyranosid) uronate)
• 英文别名: methyl (2S,3S,4S,5R,6R)-6-(3-azidopropoxy)-4,5-dibenzoyloxy-3-hydroxyoxane-2-carboxylate
• CAS: 946390-56-3
• 化学式: C₂₄H₂₅N₃O₉
• 分子量: 499.477
• InChiKey: VUVSSEUNUGLWHW-AIBQHXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-azidopropyl (methyl (2,3-di-O-benzoyl-β-D-glucopyranosid) uronate) 在 甲醇 、 二苯基亚砜 、 对甲苯磺酸 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 15.25h， 生成
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers Using Ph₂SO/Tf₂O-Mediated Glycosylations

  摘要：

  The synthesis of hyaluronic acid (HA) oligomers using a stepwise glycosylation strategy is described. This method employs protected 1-hydroxyuronic acid and 1-phenylthio glucosamine donors, both of which are activated with the Ph2SO/Tf2O activator system.

  DOI：

  10.1021/jo070704s
• 作为产物：
  描述：

  在 吡啶 、 一水合肼 、 溶剂黄146 作用下， 反应 0.25h， 以0.639 g的产率得到3-azidopropyl (methyl (2,3-di-O-benzoyl-β-D-glucopyranosid) uronate)
  参考文献：
  名称：

  Synthesis of Hyaluronic Acid Oligomers Using Ph₂SO/Tf₂O-Mediated Glycosylations

  摘要：

  The synthesis of hyaluronic acid (HA) oligomers using a stepwise glycosylation strategy is described. This method employs protected 1-hydroxyuronic acid and 1-phenylthio glucosamine donors, both of which are activated with the Ph2SO/Tf2O activator system.

  DOI：

  10.1021/jo070704s

文献信息

• Synthesis of Hyaluronic Acid Oligomers using Chemoselective and One-Pot Strategies
  作者：Jasper Dinkelaar、Henrik Gold、Herman S. Overkleeft、Jeroen D. C. Codée、Gijsbert A. van der Marel

  DOI：10.1021/jo9003713

  日期：2009.6.5

  An efficient synthetic strategy toward a hyaluronic acid (HA) tri-, penta-, and heptamer having a glucosamine-reducing end is reported. The synthesis is based on a glucuronate ester thioglycoside and a trifluoro-N-phenylimidate glucosamine building block. The HA-fragments are synthesized using an S-phenyl GlcN-GluA building block through a combination of chemoselective and one-pot condensation strategies.
• Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach
  作者：Giuseppe Macchione、José L. de Paz、Pedro M. Nieto

  DOI：10.1016/j.carres.2014.05.007

  日期：2014.7

  The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared. (C) 2014 Elsevier Ltd. All rights reserved.