4-methoxyphenyl (4,6-O-benzylidene-α-D-glucopyranosyl)-(1-->4)-β-D-glucopyranoside | 848863-37-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl (4,6-O-benzylidene-α-D-glucopyranosyl)-(1-->4)-β-D-glucopyranoside
• 英文别名: p-methoxyphenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside；4-methoxyphenyl (4,6-O-benzylidene-α-D-glucopyranosyl)-(1→4)-β-D-glucopyranoside
• CAS: 848863-37-6
• 化学式: C₂₆H₃₂O₁₂
• 分子量: 536.533
• InChiKey: LNZFLKDNLZSDMW-HXVUNDDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.54
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  165.76
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl (4,6-O-benzylidene-α-D-glucopyranosyl)-(1-->4)-β-D-glucopyranoside 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-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 在 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 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

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。
• Convergent synthesis of the tetrasaccharide repeating unit of the <i>O</i>-antigen of <i>Shigella boydii</i> type 9
  作者：Abhishek Santra、Anup Kumar Misra

  DOI：10.3762/bjoc.7.137

  日期：——

  A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic group followed by deprotection of the functional groups furnished target tetrasaccharide 1 as its 4-methoxyphenyl glycoside in high yield.

  通过使用[2+2]块状糖基化策略，成功地合成了Shigella boydii 9型O-抗原的四糖重复单元，收率非常高。对四糖衍生物8的主要醇进行TEMPO介导的选择性氧化，得到羧基，然后去保护官能团，以高收率得到目标四糖1的4-甲氧基苯基糖苷。