2-(acetoxymethyl)-5-azido-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate | 1132966-47-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(acetoxymethyl)-5-azido-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranoside；p-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-α-D-galactopyranoside；4-methoxyphenyl 3,4,5-tri-O-acetyl-2-deoxy-2-azido-D-galactopyranoside
• CAS: 1132966-47-2
• 化学式: C₁₉H₂₃N₃O₉
• 分子量: 437.406
• InChiKey: WAKAZWFEADFMAR-FQBWVUSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  155.35
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(acetoxymethyl)-5-azido-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 p-methoxyphenyl 4,6-di-O-acetyl-2-azido-2-deoxy-α-D-galactopyraside
  参考文献：
  名称：

  Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus

  摘要：

  The first stereoselective synthesis of a unique trisaccharide containing an open-chain glycosyl cyclic acetal moiety found in the cell wall of Proteus has been successfully achieved. Most of the intermediate steps are high yielding and highly reproducible. The acetal linkage of the open-chain D-galactosamine moiety with an (S)-configuration was formed exclusively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.006
• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 在 吡啶 、 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 triflic azide 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 121.5h， 生成 2-(acetoxymethyl)-5-azido-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 2-(acetoxymethyl)-5-azido-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3,4-diyl diacetate
  参考文献：
  名称：

  硫酸软骨素E（CS-E）重复单元构建的研究

  摘要：

  通过糖基化-氧化策略制备了一系列硫酸软骨素E（CS-E）二糖重复单元的衍生物。该策略在反应性和立体选择性上均表现出优异的糖基化性能。不同的保护方法被用于操纵二糖结构单元。葡萄糖基供体的C-4取代基对糖基化有轻微影响。目前的合成为CS-E重复单元的制备提供了可行的方法。

  DOI：

  10.1016/j.tet.2016.07.042

文献信息

• Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate
  作者：Haiqing He、Dong Chen、Xiaomei Li、Chengji Li、Jin-Hua Zhao、Hong-Bo Qin

  DOI：10.1039/c9ob00057g

  日期：——

  We described the chemical synthesis of a sulfated trisaccharide repeating unit of fucosylated chondroitin sulfate (FCS), which has significant anticoagulant activity. Well-functionalized monosaccharides were readily prepared, and highly efficient glycosylations using a common activator (NIS/TfOH) were also presented. The synthesized trisaccharide 4 could be used to extend oligosaccharide sequences

  我们描述了岩藻糖基硫酸软骨素（FCS）的硫酸化三糖重复单元的化学合成，其具有显着的抗凝活性。容易制备功能良好的单糖，并且还提出了使用普通活化剂（NIS / TfOH）的高效糖基化反应。合成的三糖4可用于延伸寡糖序列。
• Solvent‐Free Glycosylation from per‐ <i>O</i> ‐Acylated Donors Catalyzed by Methanesulfonic Acid
  作者：Serena Traboni、Emiliano Bedini、Alba Silipo、Giulia Vessella、Alfonso Iadonisi

  DOI：10.1002/ejoc.202101121

  日期：2021.11.8

  A novel glycosylation procedure has been developed, featuring extremely low cost as well as experimental and environmental advantages. It is based on the direct activation of per-O-acetylated (or benzoylated) sugars by 5 mol % of cheap and eco-friendly methanesulfonic acid, under air in the absence of any solvent. Several products, including non-trivial glycosides and disaccharides, can be quickly

  已经开发出一种新的糖基化程序，具有极低的成本以及实验和环境优势。它是基于直接激活per-的Ó在不存在任何溶剂的5摩尔％便宜和生态友好的甲磺酸-acetylated（或苯甲酰化）的糖，在空气下。可以快速获得具有良好 1,2-反式立体选择性的多种产品，包括重要的糖苷和二糖。