p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside | 787623-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: 4'-methylphenyl 6-O-acetyl-2,3,4-O-tribenzyl-1-thio-β-D-glucopyranoside；p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside
• CAS: 787623-80-7
• 化学式: C₃₆H₃₈O₆S
• 分子量: 598.76
• InChiKey: YLKAGKTUQGVIEU-GJXDWMKPSA-N

物化性质

• 沸点：
  698.1±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.13
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 在 2-氯吡啶 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 三氟甲磺酸酐 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.67h， 生成
  参考文献：
  名称：

  HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS

  摘要：

  糖脂类脂质（GSLs）的组成和诱导化学因子独立于iNKT的方法被揭示。

  公开号：

  US20160102116A1
• 作为产物：
  描述：

  p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 吡啶 、 甲醇 、 水 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 55.0h， 生成 p-methylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS

  摘要：

  糖脂类脂质（GSLs）的组成和诱导化学因子独立于iNKT的方法被揭示。

  公开号：

  US20160102116A1

文献信息

• HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
  申请人：Academia Sinica

  公开号：US20150071960A1

  公开（公告）日：2015-03-12

  Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and expansion and/or activation of immune cells than those with α-galactose (α-Gal) are disclosed. GSLs bearing α-glucose (α-Glc) and derivatives of α-Glc with F at the 4 and/or 6 positions are provided. Methods for iNKT-independent induction of chemokines by the GSL with α-Glc and derivatives thereof are disclosed. Methods for immune stimulation in humans using GSLs with α-Glc and derivatives thereof are provided.

  提供了带有α-葡萄糖（α-Glc）的糖脂类物质（GSLs），这些物质优先刺激人类不变NKT（iNKT）细胞。公开了具有α-葡萄糖（α-Glc）的GSLs在人类（但在小鼠中较弱）中诱导细胞因子和趋化因子以及扩张和/或激活免疫细胞的能力强于具有α-半乳糖（α-Gal）的物质。提供了带有α-葡萄糖（α-Glc）和α-Glc在4和/或6位置带有F衍生物的GSLs。公开了使用带有α-Glc及其衍生物的GSL对趋化因子进行iNKT独立诱导的方法。提供了使用带有α-Glc及其衍生物的GSL在人类中进行免疫刺激的方法。
• A flexible 1,2-cis α-glycosylation strategy based on in situ adduct transformation
  作者：Jhe-Cyuan Hu、Ai-Fen Wendy Feng、Bo-Yao Chang、Chun-Hung Lin、Kwok-Kong Tony Mong

  DOI：10.1039/c7ob00839b

  日期：——

  strategy for a wide range of glycosyl donors and acceptors has been developed, which is based on an in situ adduct transformation protocol. Based on this strategy, both NFM-derived and iodide covalent adducts can be accessed for glycosylation. Using low temperature NMR spectroscopy, the aforementioned glycosyl adducts were detected.

  已经开发了一种针对多种糖基供体和受体的灵活的1,2-顺式α-选择性糖基化策略，该策略基于原位加合物转化方案。基于此策略，可以获取NFM衍生品和碘化物共价加合物进行糖基化。使用低温NMR光谱法，检测到上述糖基加合物。
• Synthesis of Pentasaccharide Repeating Unit Corresponding to the Cell Wall O-Polysaccharide of Salmonella enterica O55 Strain Containing a Rare Sugar 3-Acetamido-3-deoxy-d-fucose
  作者：Anup Kumar Misra、Arin Gucchait、Monalisa Kundu

  DOI：10.1055/s-0037-1610777

  日期：2021.10

  A pentasaccharide repeating unit corresponding to the cell wall O-antigen of Salmonella enterica O55 containing a rare sugar, 3-acetamido-3-deoxy-d-fucose has been synthesized as its p-methoxyphenyl glycoside using a sequential stereoselective glycosylation strategy. A suitably functionalized 3-azido-3-deoxy-d-fucose thioglycoside derivative was prepared in very good yield and used in the stereoselective

  一种五糖重复单元，对应于肠道沙门氏菌O55 的细胞壁O-抗原，含有稀有糖，3-乙酰氨基-3-脱氧-d-岩藻糖已使用顺序立体选择性糖基化策略合成为对甲氧基苯基糖苷。适当官能化的 3-azido-3-deoxy-d-岩藻糖硫糖苷衍生物以非常好的收率制备并用于立体选择性糖基化反应。明智地制备功能化单糖中间体并进行立体选择性组装，以优异的收率获得所需的五糖衍生物。
• A mild method for regioselective de-O-methylation of saccharides by Co2(CO)8/Et3SiH/CO system
  作者：Yue-tao Zhao、Lu-bai Huang、Qing Li、Zhong-jun Li

  DOI：10.1016/j.tet.2016.07.081

  日期：2016.9

  A new method for cleaving methyl ethers off protected saccharides using Co2(CO)8/Et3SiH/CO system was developed. The method showed regioselectivity in different protected monosaccharides with various anomeric groups. The primary and equatorial secondary methyl ethers were preferentially removed. This method was successfully applied to the synthesis of the DEF trisaccharide segment of Idraparinux, which

  开发了一种利用Co 2（CO）8 / Et 3 SiH / CO系统从保护糖上裂解甲基醚的新方法。该方法在具有各种异头基团的不同受保护单糖中显示区域选择性。优先除去伯和赤道仲甲基醚。此方法已成功应用于高度甲基化的伊德拉帕林的DEF三糖链段的合成。
• [EN] STABLE VACCINE AGAINST CLOSTRIDIUM DIFFICILE<br/>[FR] VACCIN STABLE DIRIGÉ CONTRE CLOSTRIDIUM DIFFICILE
  申请人：VAXXILON AG

  公开号：WO2020104697A1

  公开（公告）日：2020-05-28

  The present invention relates to a synthetic saccharide of general formula (I) that is related to Clostridium difficile PS-II cell-surface polysaccharide and conjugate thereof. Said synthetic saccharide, said conjugate and pharmaceutical composition containing said synthetic saccharide or said conjugate are useful for prevention and/or treatment of diseases associated with Clostridium difficile. Furthermore, the synthetic saccharide of general formula (I) is useful as marker in immunological assays for detection of antibodies against Clostridium difficile bacteria.

  本发明涉及一种与Clostridium difficile PS-II细胞表面多糖及其共轭物相关的通用式(I)的合成糖苷。所述合成糖苷，所述共轭物以及含有所述合成糖苷或所述共轭物的药物组合物对于预防和/或治疗与Clostridium difficile相关的疾病是有用的。此外，通用式(I)的合成糖苷在免疫学检测中作为标记物是有用的，用于检测针对Clostridium difficile细菌的抗体。