p-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside | 258333-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS: 258333-93-6
• 化学式: C₂₄H₂₆O₇S
• 分子量: 458.532
• InChiKey: BKNQELQNPOSQPY-IPJQNIFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 硼烷四氢呋喃络合物 、 三氟甲磺酸 、 三氟甲磺酸二丁硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.17h， 生成 benzyl 2,3,6-tri-O-acetyl-4-O-benzyl-β-D-galactopyranosyl-(1→4)-2,3-di-O-benzyl-6-O-para-methoxybenzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Modular synthesis and immunological evaluation of suspected allergenic galactooligosaccharides

  摘要：

  报告了使用灵活的模块化方法合成疑似GOS相关过敏原并对其进行免疫学评估。

  DOI：

  10.1039/c9ob00108e
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 p-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-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

• Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation
  作者：Jyun-Siao Chen、Arumugam Sankar、Yi-Jyun Lin、Po-Hsun Huang、Chih-Hsiang Liao、Shen-Shen Wu、Hsin-Ru Wu、Shun-Yuan Luo

  DOI：10.1039/c9ra06170c

  日期：——

  phosphotungstic acid solely for different carbohydrate reactions. It can be widely used as a catalyst for organic reactions as it is thermally stable and easy to handle. In our work, the reactions are operated smoothly under ambient conditions; the temperature varies from 0 °C to room temperature. Good to excellent yields were obtained in all four kinds of reactions.

  这项工作展示了磷钨酸（PTA）作为碳水化合物反应的新型酸性催化剂的用途，例如全O-乙酰化、区域选择性O -4,6 亚苄基缩醛形成、区域选择性O -4 开环和糖基化。这些反应在碳水化合物基生物活性低聚物的合成过程中是基本且重要的。磷钨酸的高酸度和环保特性使其成为腐蚀性均质酸的诱人替代品。仅针对不同的碳水化合物反应，用磷钨酸代替各种均相酸催化剂。由于其热稳定且易于处理，可广泛用作有机反应的催化剂。在我们的工作中，反应在环境条件下顺利进行；温度从 0 °C 到室温变化。所有四种反应均获得良好至优异的产率。
• Tandem One-Pot Acetalation-Acetylation for Direct Access to Differentially Protected Thioglycosides and O-Glycosides with p-Toluenesulfonic Acid
  作者：Kwok-Kong Mong、Chin-Sheng Chao、Min-Chun Chen、Chun-Wei Lin

  DOI：10.1055/s-0028-1087913

  日期：2009.3

  A new tandem one-pot acetalation-acetylation procedure is reported which streamlines routine protecting-group manipulation of carbohydrate molecules in production of differentially protected O- and thioglycosides. This new procedure eliminates the use of highly toxic pyridine, and p-toluenesulfonic acid is employed as catalyst for acetalation and acetylation. Synthetic utility of the new procedure is demonstrated in the expeditious preparation of differentially protected glycosides from a wide variety of carbohydrate substrates including unprotected O-glycosides, thioglycosides, and N-acetyl neuraminic acid ester.

  报道了一种新的串联一锅缩醛化-乙酰化程序，该程序简化了在生产差异保护的 O- 和硫代糖苷时碳水化合物分子的常规保护基操作。这种新工艺消除了剧毒吡啶的使用，并采用对甲苯磺酸作为缩醛化和乙酰化的催化剂。新方法的合成效用在从多种碳水化合物底物（包括未保护的 O-糖苷、硫代糖苷和 N-乙酰神经氨酸酯）快速制备差异保护糖苷方面得到了证明。