(2-methyl-5-tert-butylphenyl) 1-thio-β-D-glucopyranose | 1421758-31-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methyl-5-tert-butylphenyl) 1-thio-β-D-glucopyranose
• 英文别名: (2-methyl-5-tert-butylphenyl) 1-thio-ß-D-glucopyranoside；(2-methyl-5-tert-butylphenyl) 1-thio-β-D-glucopyranoside；(2-Methyl-5-tert-butylphenyl) 1-thio-beta-D-glucopyranoside；(2S,3R,4S,5S,6R)-2-(5-tert-butyl-2-methylphenyl)sulfanyl-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1421758-31-7
• 化学式: C₁₇H₂₆O₅S
• 分子量: 342.456
• InChiKey: PWMRGTXMBSQPAT-JZYAIQKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-methyl-5-tert-butylphenyl) 1-thio-β-D-glucopyranose 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 2,3,4-tri-O-benzoyl-β-D-glucopyranosyl (Z)-3-iodoacrylate
  参考文献：
  名称：

  金（I）催化的糖基壬二酸酯作为供体的糖基化

  摘要：

  开发了一种简单且通用的糖基化方法，其中武装和解除武装的糖基炔诺酸酯都作为供体。在有或没有TfOH的辅助下采用金（I）配合物作为催化剂，本糖基化方案的范围非常宽。通过潜在的活性策略和多重正交一锅策略在低聚糖的有效合成中证明了本发明的炔酸供体的实用性。最后，该方法能够正式合成肺炎链球菌血清型3的四糖半抗原和32mer聚甘露糖苷的高度收敛合成。

  DOI：

  10.1021/acs.orglett.9b03851
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2-methyl-5-tert-butylphenyl) 1-thio-β-D-glucopyranose
  参考文献：
  名称：

  Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: synthesis of the cell-surface polysaccharide PS-I repeating unit

  摘要：

  克劳斯特里迪姆·迪菲西尔株核糖型027是一种高度毒力病原体，导致了最近严重的医院感染暴发。作为开发基于碳水化合物的预防性疫苗的基础，我们通过对四种单糖构件进行线性组合，合成了该株特有的PS-I五糖细胞壁重复单元。

  DOI：

  10.1039/c1cc13614c

文献信息

• Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: synthesis of the cell-surface polysaccharide PS-I repeating unit
  作者：Christopher E. Martin、Markus W. Weishaupt、Peter H. Seeberger

  DOI：10.1039/c1cc13614c

  日期：——

  Clostridium difficile strain ribotype 027 is a hypervirulent pathogen that is responsible for recent, severe outbreaks of serious nosocomial infections. As a foundation for the development of a preventative carbohydrate-based vaccine, we have synthesized a pentasaccharide cell wall repeating unit from PS-I unique to this strain, by the linear assembly of four monosaccharide building blocks.

  克劳斯特里迪姆·迪菲西尔株核糖型027是一种高度毒力病原体，导致了最近严重的医院感染暴发。作为开发基于碳水化合物的预防性疫苗的基础，我们通过对四种单糖构件进行线性组合，合成了该株特有的PS-I五糖细胞壁重复单元。
• [EN] OLIGOSACCHARIDES AND OLIGOSACCHARIDE-PROTEIN CONJUGATES DERIVED FROM CLOSTRIDIUM DIFFICILE POLYSACCARIDE PS-I, METHODS OF SYNTHESIS AND USES THEREOF, IN PARTICULAR AS VACCINES AND DIAGNOSTIC TOOLS<br/>[FR] OLIGOSACCHARIDES ET CONJUGUÉS D'OLIGOSACCHARIDES-PROTÉINES PROVENANT DE POLYSACCARIDES PS-I DE CLOSTRIDIUM DIFFICILE, LEURS PROCÉDÉS DE SYNTHÈSE ET D'UTILISATION, EN PARTICULIER EN TANT QUE VACCINS ET OUTILS DE DIAGNOSTIC
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2013017254A1

  公开（公告）日：2013-02-07

  The invention relates to a synthetic oligosaccharide representing part of the repeating unit of the Clostridium difficile glycopolymer PS-I and having the sequence of the pentasaccharide a-L-Rhap- ( 1→3 ) -β-D-Glcp- ( 1→4 ) - [a-L-Rhap- ( 1→3 ] -a-D-Glcp- ( 1→2 ) -a-D-Glcp or a synthetic fragment or derivative thereof. Preferably, the claimed synthetic oligosaccharide bears at least one linker L for conjugation to a carrier protein or for immobilization on a surface. Further aspects of the invention relate to advantageous methods for synthesizing said synthetic oligosaccharide and oligosaccharide-protein conjugate as well as to uses thereof, in particular as vaccines and diagnostic tools.

  该发明涉及一种合成的寡糖，代表Clostridium difficile糖聚合物PS-I的重复单元的一部分，并具有五糖基序列a-L-Rhap-（1→3）-β-D-Glcp-（1→4）-[a-L-Rhap-（1→3]-a-D-Glcp-（1→2）-a-D-Glcp或其合成片段或衍生物。优选，所述的合成寡糖至少带有一个连接子L，用于与载体蛋白共轭或固定在表面上。该发明的进一步方面涉及有利的合成所述合成寡糖和寡糖-蛋白共轭的方法，以及它们的用途，特别是作为疫苗和诊断工具。
• Oligosaccharides and oligosaccharides-protein conjugates derived from clostridium difficile polysaccharide PS-I, methods of synthesis and uses thereof, in particular as vaccines and diagnostic tools
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2554549A1

  公开（公告）日：2013-02-06

  The invention relates to a synthetic oligosaccharide representing part of the repeating unit of the Clostridium difficile glycopolymer PS-I and having the sequence of the pentasaccharide α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→2)-α-D-Glcp or a synthetic fragment or derivative thereof. Preferably, the claimed synthetic oligosaccharide bears at least one linker L for conjugation to a carrier protein or for immobilization on a surface. Further aspects of the invention relate to advantageous methods for synthesizing said synthetic oligosaccharide and oligosaccharide-protein conjugate as well as to uses thereof, in particular as vaccines and diagnostic tools. A preferred method for synthesizing the pentasaccharide is shown below.

  该发明涉及一种合成的寡糖，代表Clostridium difficile糖聚合物PS-I的重复单元的一部分，并具有五糖基序列α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→2)-α-D-Glcp或其合成片段或衍生物。优选，所述的合成寡糖至少带有一个连接体L，用于与载体蛋白结合或在表面上固定。该发明的其他方面涉及有利的合成所述合成寡糖和寡糖-蛋白共轭物的方法，以及它们的用途，特别是作为疫苗和诊断工具。下面显示了一种合成五糖基的首选方法。
• OLIGOSACCHARIDES AND OLIGOSACCHARIDE-PROTEIN CONJUGATES DERIVED FROM CLOSTRIDIUM DIFFICLE POLYSACCARIDE PS-I, METHODS OF SYNTHESIS AND USES THEREOF, IN PARTICULAR AS VACCINES AND DIAGNOSTIC TOOLS
  申请人：Seeberger Peter H.

  公开号：US20140193416A1

  公开（公告）日：2014-07-10

  The invention relates to a synthetic oligosaccharide representing part of the repeating unit of the Clostridium difficile glycopolymer PS-I and having the sequence of the pentasaccharide a-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[a-L-Rhap-(1→3]-a-D-Glcp-(1→2)-a-D-Glcp or a synthetic fragment or derivative thereof. Preferably, the claimed synthetic oligosaccharide bears at least one linker L for conjugation to a carrier protein or for immobilization on a surface. Further aspects of the invention relate to advantageous methods for synthesizing said synthetic oligosaccharide and oligosaccharide-protein conjugate as well as to uses thereof, in particular as vaccines and diagnostic tools.

  本发明涉及一种合成寡糖，其代表Clostridium difficile糖聚合物PS-I重复单元的一部分，并具有五糖核苷酸序列a-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[a-L-Rhap-(1→3]-a-D-Glcp-(1→2)-a-D-Glcp或其合成片段或衍生物。优选地，所述合成寡糖至少带有一种连接物L，用于与载体蛋白质结合或固定在表面上。本发明的其他方面涉及有利的方法，用于合成所述合成寡糖和寡糖-蛋白质结合物，以及其用途，特别是作为疫苗和诊断工具。
• Oligosaccharides and oligosaccharide-protein conjugates derived from Clostridium difficile polysaccharide PS-I, methods of synthesis and uses thereof, in particular as vaccines and diagnostic tools
  申请人：Seeberger Peter H.

  公开号：US09238669B2

  公开（公告）日：2016-01-19

  The invention relates to a synthetic oligosaccharide representing part of the repeating unit of the Clostridium difficile glycopolymer PS-I and having the sequence of the pentasaccharide a-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[a-L-Rhap-(1→3]-a-D-Glcp-(1→2)-a-D-Glcp or a synthetic fragment or derivative thereof. Preferably, the claimed synthetic oligosaccharide bears at least one linker L for conjugation to a carrier protein or for immobilization on a surface. Further aspects of the invention relate to advantageous methods for synthesizing said synthetic oligosaccharide and oligosaccharide-protein conjugate as well as to uses thereof, in particular as vaccines and diagnostic tools.

  本发明涉及一种合成寡糖，它代表Clostridium difficile糖聚合物PS-I重复单元的一部分，并具有五糖的序列a-L-Rhap-(1→3)-β-D-Glcp-(1→4)-[a-L-Rhap-(1→3]-a-D-Glcp-(1→2)-a-D-Glcp或其合成片段或衍生物。优选地，所述合成寡糖至少带有一种连接物L，用于与载体蛋白质结合或固定在表面上。本发明的其他方面涉及有利的方法，用于合成所述合成寡糖和寡糖-蛋白质结合物，以及它们的用途，特别是作为疫苗和诊断工具。