p-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside | 848863-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside
• 英文别名: b-D-Glucopyranoside, 4-methoxyphenyl4-O-(2,3,4,6-tetra-O-acetyl-a-D-glucopyranosyl)-, triacetate；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-(4-methoxyphenoxy)-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 848863-34-3
• 化学式: C₃₃H₄₂O₁₉
• 分子量: 742.685
• InChiKey: CHQFKIZJLSSYAP-RCQOQWBPSA-N

物化性质

• 熔点：
  206-208 °C(Solv: ethanol (64-17-5))
• 沸点：
  738.9±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  230
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 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 12.0h， 生成 4-methoxyphenyl (4,6-O-benzylidene-α-D-glucopyranosyl)-(1-->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides

  摘要：

  Analysis of glycosylation stercoselectivity in the synthesis of branched maltooligosaccharides is hampered by poor spectral dispersion due to the repetitive nature of the saccharide chain and overlap of sugar H-l signals with benzylic proton signals from the typically used benzyl ether protecting groups. A suitably protected p-methoxyphenyl maltoside acceptor, when coupled with benzylated maltooligosaccharide donors, gives discrete aglycone H-1 NMR signals that can be used to report on the stereo selectivity of 1,6-glycosylation reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.047
• 作为产物：
  描述：

  4-甲氧基苯酚 、 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以74%的产率得到p-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Lanthanum Trifluoromethane-sulfonate‐Catalyzed Facile Synthesis of Per‐O‐acetylated Sugars and Their One‐Pot Conversion to S‐Aryl and O‐Alkyl/Aryl Glycosides

  摘要：

  Lanthanum trifluoromethanesulfonate- catalyzed solvent-freeper-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.[GRAPHICS]

  DOI：

  10.1080/07328300701298170

文献信息

• 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。
• “Click chemistry”en route to pseudo-starch
  作者：Laurence Marmuse、Sergey A. Nepogodiev、Robert A. Field

  DOI：10.1039/b504293c

  日期：——

  Rapid assembly of starch fragment analogues was achieved using “click chemistry”. Specifically, two hexadecasaccharide mimics containing two parallel maltoheptaosyl chains linked via [1,2,3]-triazoles to a maltose core were synthesized using Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of azido saccharides and 6,6′- and 4′,6′-dipropargylated p-methoxyphenyl maltoside.

  使用“点击化学”实现了淀粉片段类似物的快速组装。具体来说，使用 Cu(I) 催化的叠氮糖的 [3 + 2] 偶极环加成反应合成了两种十六糖模拟物，其中包含通过 [1,2,3]-三唑连接到麦芽糖核心的两条平行的麦芽七糖基链和 6,6−2 - 和 4α,6α-二炔丙基化对甲氧基苯基麦芽糖苷。
• Synthesis of triazole-linked pseudo-starch fragments
  作者：Sergey A. Nepogodiev、Simone Dedola、Laurence Marmuse、Marcelo T. de Oliveira、Robert A. Field

  DOI：10.1016/j.carres.2006.09.026

  日期：2007.2

  Rapid assembly of starch fragment analogues was achieved using 'click chemistry'. Specifically, a pentadecasaccharide and two hexadecasaccharide mimics containing two parallel maltoheptaosyl chains linked via [1,2,3]-triazoles to glucose or maltose core were synthesised using Cu(l)-catalyzed [3+2] dipolar cycloaddition of azidosaccharides and 4,6-di-O-propargylated methyl alpha-D-glucopyranoside and 6,6'- and 4',6'-di-O-propargylated p-methoxyphenyl beta-maltoside. (c) 2006 Elsevier Ltd. All rights reserved.