p-methoxyphenyl 2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside | 620172-07-8

• 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-di-O-benzoyl-1-thio-β-D-galactopyranoside
• 英文别名: p-methylphenyl 2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside；p-tolyl 2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside；p-methylphenyl-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside；[(2R,3S,4S,5R,6S)-5-benzoyloxy-3-hydroxy-2-(hydroxymethyl)-6-(4-methylphenyl)sulfanyloxan-4-yl] benzoate
• CAS: 620172-07-8
• 化学式: C₂₇H₂₆O₇S
• 分子量: 494.565
• InChiKey: HADJRSOKOACEBB-PFGYYQCGSA-N

物化性质

• 沸点：
  694.2±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 作用下， 以 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.75h， 生成
  参考文献：
  名称：

  合成氨基糖苷的双重作用：对炭疽芽孢杆菌的抗菌活性和对炭疽致死因子的抑制作用。

  摘要：

  DOI：

  10.1002/anie.200462003
• 作为产物：
  描述：

  p-tolyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Programmable One-Pot Oligosaccharide Synthesis

  摘要：

  In an effort to develop a broadly applicable approach to the facile one-pot synthesis of oligosaccharides, the reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We have characterized and quantified the influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor. In addition, we have established a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by H-1 NMR. Using the reactivity data, we have created a database of thioglycosides as glycosyl donors and demonstrated its utility in the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures. In addition, we have developed the first computer program, OptiMer, for use as a database search tool and guide for the selection of building blocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.

  DOI：

  10.1021/ja982232s

文献信息

• Bifunctional antibiotics for targeting rRNA and resistance-causing enzymes
  申请人：Baasov Timor

  公开号：US20050004052A1

  公开（公告）日：2005-01-06

  A novel group of aminoglycosides which share some structural features of currently available aminoglycosides with regard to the backbone, while also having significant structural differences. The similarity enables these aminoglycosides to be highly potent and effective antibiotics, while the significant differences enable these aminoglycosides to reduce or even block antibiotic resistance.

  一种新型氨基糖苷类药物，与目前已有的氨基糖苷类药物在骨架方面具有一些结构特征，同时又具有显著的结构差异。这种相似性使得这些氨基糖苷类药物具有很高的抗菌作用和有效性，而显著的差异使得这些氨基糖苷类药物能够减少甚至阻止抗生素耐药性的发展。
• Highly Alpha-Selective Sialyl Phosphate Donors for Efficient Preparation of Natural Sialosides
  作者：Che-Hsiung Hsu、Kuo-Ching Chu、Yih-Shyan Lin、Jeng-Liang Han、Yu-Shiang Peng、Chien-Tai Ren、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1002/chem.200903035

  日期：2010.2.8

  Hubble, bubble, toil, and trouble: The use of a new sialyl phosphate donor allows the stereoselective, one‐pot multicomponent synthesis of α‐sialooligosaccharides (see scheme).

  哈勃，气泡，辛劳和麻烦：使用新的唾液酸磷酸酯供体可以立体选择性地单锅多组分合成α-唾液寡糖（参见方案）。
• Stereodirecting Effects of <scp> 4‐ <i>O</i> </scp> ‐ <i>ortho</i> ‐cyanobenzyl Ether on Chemical Glycosylation with Glucopyranosyl Donor
  作者：Han Zhang、Aoxin Guo、Youhui Meng、Yue Wang、Jian Gao、Xue‐Wei Liu

  DOI：10.1002/cjoc.202200595

  日期：2023.3.15

  4-O-ortho-cyanobenzyl ether (oBCN) group with a glucopyranosyl donor. Experimental studies revealed that the glycosylation reactions using this donor generally show dual-stereoselectivities depending on the acceptor nucleophilicity, that is, glycosylation of weak nucleophile acceptors generally affords α-glycosides specifically while glycosylation of strong nucleophile acceptors affords β-glycosides preferentially

  在这里，我们报告了一项关于 4- O -邻氰基苄基醚 ( o BCN) 基团与吡喃葡萄糖供体的立体定向效应的系统研究。实验研究表明，使用该供体的糖基化反应通常表现出双立体选择性，这取决于受体的亲核性，即弱亲核受体的糖基化通常特异性提供 α-糖苷，而强亲核受体的糖基化优先提供 β-糖苷。DFT 计算表明，强亲核试剂优先攻击 S N中主要的共价 α-糖基三氟甲磺酸酯中间体2-like 方式，而弱亲核试剂优先攻击稳定性较差且反应性较高的 β-糖基三氟甲磺酸酯，具有氢键介导的方向。血清型 IV 组 B链球菌荚膜多糖的六糖重复单元的首次简便合成证明了在碳水化合物化学中具有o BCN 功能的葡糖基结构单元的多功能用途。
• Bifunctional antibiotics for targeting rRNA and resistance-causing enzymes and for inhibition of anthrax lethal factor
  申请人：Baasov Timor

  公开号：US20050148522A1

  公开（公告）日：2005-07-07

  A novel group of aminoglycosides which share some structural features of currently available aminoglycosides with regard to the backbone, while also having significant structural differences, is disclosed. The similarity enables these aminoglycosides to be highly potent and effective antibiotics, while the significant differences enable these aminoglycosides to reduce or even block antibiotic resistance. The aminoglycosides of the present invention are suitable for inhibition of antrax lethal factor, hence are suitable for use as a cure for anthrax.

  本研究揭示了一组新型氨基糖苷类药物，它们在骨架方面与现有的氨基糖苷类药物具有一些相同的结构特征，同时在结构上也有显著差异。相似性使这些氨基糖苷类药物成为强效和有效的抗生素，而显著的差异则使这些氨基糖苷类药物能够减少甚至阻止抗生素耐药性的产生。本发明的氨基糖苷类药物适用于抑制抗炭疽致死因子，因此适用于治疗炭疽。
• Roy, Samarpita; Sarkar, Sujit Kumar; Roy, Nirmolendu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 1, p. 137 - 140
  作者：Roy, Samarpita、Sarkar, Sujit Kumar、Roy, Nirmolendu

  DOI：——

  日期：——