4-methoxyphenyl (α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside
• 英文别名: D-Glc-α-(1->4)-D-Glc-β-OMP；Glc(a1-4)Glc(b)-O-Ph(4-OMe)；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-methoxyphenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₁₉H₂₈O₁₂
• 分子量: 448.424
• InChiKey: PJFQMORRZLJWQE-CRINDFDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  188
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside 在 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 p-methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  “Click chemistry”en route to pseudo-starch

  摘要：

  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。

  DOI：

  10.1039/b504293c
• 作为产物：
  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 作用下， 以 甲醇 为溶剂， 生成 4-methoxyphenyl (α-D-glucopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  “Click chemistry”en route to pseudo-starch

  摘要：

  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。

  DOI：

  10.1039/b504293c

文献信息

• Efficient one-pot per-O-acetylation–thioglycosidation of native sugars, 4,6-O-arylidenation and one-pot 4,6-O-benzylidenation–acetylation of S-/O-glycosides catalyzed by Mg(OTf)₂
  作者：Mana Mohan Mukherjee、Nabamita Basu、Aritra Chaudhury、Rina Ghosh

  DOI：10.1039/c6ra23198e

  日期：——

  A sequential one-pot per-O-acetylation–S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated

  据报道，在无溶剂条件下，使用0.5摩尔％的Mg（OTf）2作为非吸湿性，可循环利用的催化剂，对单糖和双糖进行连续一锅过O-乙酰化– S- / O-糖基化反应。糖苷和硫糖苷与苯甲醛或对甲氧基苯甲醛二甲基乙缩醛的区域选择性4,6- O-芳基化反应可通过10摩尔％的Mg（OTf）2催化生成相应的4,6- O-芳基化产物。Mg（OTf）2也可以高产率地介导单糖和二糖基糖苷和硫代糖苷的顺序一锅苯甲基化-乙酰化。
• Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides
  作者：Laurence Marmuse、Sergey A. Nepogodiev、Robert A. Field

  DOI：10.1016/j.tetasy.2004.11.047

  日期：2005.1

  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.
• FeCl3 mediated arylidenation of carbohydrates
  作者：Nabamita Basu、Sajal K. Maity、Soumik Roy、Shuvendu Singha、Rina Ghosh

  DOI：10.1016/j.carres.2011.01.003

  日期：2011.4

  Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-0-arylidenation producing the corresponding acetals in high yields. FeCl3 also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4',6'-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn. (C) 2011 Elsevier Ltd. All rights reserved.
• Tanikawa, Tetsuya; Fridman, Micha; Zhu, Wenjiang, Journal of the American Chemical Society, 2009, vol. 131, p. 5075 - 5083
  作者：Tanikawa, Tetsuya、Fridman, Micha、Zhu, Wenjiang、Faulk, Brian、Joseph, Isaac C.、et al.

  DOI：——

  日期：——
• 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.