p-tolyl 2,3-di-O-benzoyl-1-thio-β-D-xylopyranose | 1415218-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-tolyl 2,3-di-O-benzoyl-1-thio-β-D-xylopyranose
• 英文别名: 1-(4-tolyl)thio-2,3-di-O-benzoyl-4-β-D-xylopyranoside；4-methylphenyl 2,3-di-O-benzoyl-1-thio-β-D-xylopyranoside；[(2S,3R,4S,5R)-3-benzoyloxy-5-hydroxy-2-(4-methylphenyl)sulfanyloxan-4-yl] benzoate
• CAS: 1415218-09-5
• 化学式: C₂₆H₂₄O₆S
• 分子量: 464.539
• InChiKey: ZKJYPDJLJPNBHC-VUMQFKOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3-di-O-benzoyl-1-thio-β-D-xylopyranose 在 N-溴代丁二酰亚胺(NBS) 、 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 3.58h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate
  参考文献：
  名称：

  Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives

  摘要：

  Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of alpha-L-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C-3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, alpha-L-rhamnosyl moiety linked to C-2-OH of the first monosaccharide (alpha-L-alabinose, beta-D-xylose, beta-n-galactose or beta-D-glucose) in C-3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.016
• 作为产物：
  描述：

  D-吡喃木糖 在 吡啶 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 22.0h， 生成 p-tolyl 2,3-di-O-benzoyl-1-thio-β-D-xylopyranose
  参考文献：
  名称：

  硫酸乙酰肝素糖肽的化学合成：Syndecan-1

  摘要：

  首先完成：组装了标题化合物的高度复杂结构（见图）。所使用的保护基团以及用于形成糖基连接和保护基团去除的序列对于合成的成功至关重要。硫酸乙酰肝素糖肽的首次制备为获得此类分子的其他成员奠定了基础。

  DOI：

  10.1002/anie.201205601

文献信息

• Tailormade Polysaccharides with Defined Branching Patterns: Enzymatic Polymerization of Arabinoxylan Oligosaccharides
  作者：Deborah Senf、Colin Ruprecht、Saina Kishani、Aleksandar Matic、Guillermo Toriz、Paul Gatenholm、Lars Wågberg、Fabian Pfrengle

  DOI：10.1002/anie.201806871

  日期：2018.9.10

  nature of non‐cellulosic polysaccharides, such as arabinoxylan, makes it difficult to correlate molecular structure with macroscopic properties. To study the impact of specific structural features of the polysaccharides on crystallinity or affinity to other cell wall components, collections of polysaccharides with defined repeating units are required. Herein, a chemoenzymatic approach to artificial

  非纤维素多糖（如阿拉伯木聚糖）的异质性使得难以将分子结构与宏观特性相关联。为了研究多糖的特定结构特征对结晶度或对其他细胞壁成分的亲和力的影响，需要收集具有确定的重复单元的多糖。在本文中，描述了化学酶促方法来制备具有系统地改变的分支模式的人工阿拉伯木聚糖多糖。多糖是通过糖合酶催化的阿拉伯糖基木聚糖寡糖衍生的糖基氟化物聚合而获得的。纤维素表面的X射线衍射和吸附实验表明，合成多糖的理化性质强烈取决于其取代模式的特定性质。人造多糖允许进行其他方法无法访问的结构与性质之间的关系研究。
• Chemical synthesis of human syndecan-4 glycopeptide bearing O-, N-sulfation and multiple aspartic acids for probing impacts of the glycan chain and the core peptide on biological functions
  作者：Weizhun Yang、Yigitcan Eken、Jicheng Zhang、Logan Emerson Cole、Sherif Ramadan、Yongmei Xu、Zeren Zhang、Jian Liu、Angela K. Wilson、Xuefei Huang

  DOI：10.1039/d0sc01140a

  日期：——

  homogeneous proteoglycan glycopeptides are needed. Herein, we report the first successful synthesis of proteoglycan glycopeptides bearing multiple aspartic acids in the core peptide and O- and N-sulfations in the glycan chain, as exemplified by the syndecan-4 glycopeptides. To overcome the high acid sensitivities of sulfates and base sensitivities of the glycopeptide during synthesis, a new synthetic approach

  蛋白聚糖是一类复杂的糖蛋白，其糖胺聚糖链如硫酸乙酰肝素 (HS) 连接到核心蛋白主链上。由于 HS 在自然界中的高度结构异质性，破译 HS 链和核心蛋白对蛋白多糖功能的各自作用具有挑战性。虽然 HS 的硫酸化模式决定了许多活动，但核心蛋白可能会影响 HS 功能。为了破译这一点，需要均质的蛋白聚糖糖肽。在此，我们报告了在核心肽中带有多个天冬氨酸并在聚糖链中带有 O- 和 N- 硫酸盐的蛋白多糖糖肽的首次成功合成，例如 syndecan-4 糖肽。为了克服合成过程中硫酸盐的高酸敏感性和糖肽的碱敏感性，已开发出一种新的合成方法，可在易于形成阿斯巴酰亚胺副产物的肽序列上产生硫酸化聚糖链。结构明确的合成糖肽的可用性使得能够研究其生物学功能，包括细胞因子、生长因子结合和乙酰肝素酶抑制。有趣的是，与单独的肽或聚糖相比，糖肽表现出依赖于上下文的生物活性增强或降低。本文提供的结果表明，除了改变 HS 的硫酸化模式之外，将
• Chemical Synthesis of a Heparan Sulfate Glycopeptide: Syndecan-1
  作者：Bo Yang、Keisuke Yoshida、Zhaojun Yin、Hang Dai、Herbert Kavunja、Mohammad H. El-Dakdouki、Suttipun Sungsuwan、Steven B. Dulaney、Xuefei Huang

  DOI：10.1002/anie.201205601

  日期：2012.10.1

  assembled. The protective groups utilized, as well as the sequences for formation of the glycosyl linkages and protecting group removal are critical to the success of the synthesis. This first preparation of a heparan sulfate glycopeptide lays the foundation for accessing other members of this class of molecules.

  首先完成：组装了标题化合物的高度复杂结构（见图）。所使用的保护基团以及用于形成糖基连接和保护基团去除的序列对于合成的成功至关重要。硫酸乙酰肝素糖肽的首次制备为获得此类分子的其他成员奠定了基础。
• Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives
  作者：Qingchao Liu、Hongchun Liu、Lei Zhang、Tiantian Guo、Peng Wang、Meiyu Geng、Yingxia Li

  DOI：10.1016/j.ejmech.2013.04.016

  日期：2013.6

  Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of alpha-L-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was important to enhance cytotoxicity, and introducing more sugar residues at C-3-OH of compound 12 with C-28 carboxylic acid is a favorable modification to ameliorate the anticancer activity. Furthermore, alpha-L-rhamnosyl moiety linked to C-2-OH of the first monosaccharide (alpha-L-alabinose, beta-D-xylose, beta-n-galactose or beta-D-glucose) in C-3-OH of oleanolic acid was helpful to improve the cytotoxicity. According to the predicted log P values, lipophilicity of the synthesized saponins was not an important factor for cytotoxicity. (C) 2013 Elsevier Masson SAS. All rights reserved.