ethyl 4-O-benzoyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside | 1352827-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-O-benzoyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• CAS: 1352827-02-1
• 化学式: C₃₆H₃₈O₆S
• 分子量: 598.76
• InChiKey: OQRGNZAPLDELGL-QOKMRYHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 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：

  ethyl 4-O-benzoyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以70%的产率得到4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl bromide
  参考文献：
  名称：

  Glycosidation of Thioglycosides in the Presence of Bromine: Mechanism, Reactivity, and Stereoselectivity

  摘要：

  Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that beta-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, alpha-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into alpha-bromide that is totally unreactive under the established reaction conditions.

  DOI：

  10.1021/jo2019174
• 作为产物：
  描述：

  苯甲酰氯 、 乙基 2,3,6-O-三苄基-beta-D-硫代吡喃葡萄糖苷 在 吡啶 作用下， 反应 1.0h， 以89%的产率得到ethyl 4-O-benzoyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosidation of Thioglycosides in the Presence of Bromine: Mechanism, Reactivity, and Stereoselectivity

  摘要：

  Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that beta-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, alpha-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into alpha-bromide that is totally unreactive under the established reaction conditions.

  DOI：

  10.1021/jo2019174

文献信息

• [EN] PNEUMOCOCCAL POLYSACCHARIDE-PROTEIN CONJUGATE COMPOSITION<br/>[FR] COMPOSITION DE CONJUGUÉ POLYSACCHARIDE PNEUMOCOCCIQUE-PROTÉINE
  申请人：MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WSS E V

  公开号：WO2017220753A1

  公开（公告）日：2017-12-28

  The present invention relates to immunogenic compositions comprising a conjugate of a saccharide from Streptococcus pneumoniae serotype 8 and a carrier protein, and a mixture consisting of capsular polysaccharides from Streptococcus pneumoniae serotypes 1, 3, 4, 5, 6A, 6B, 7F, 9V, 14, 18C, 19A, 19F and 23F individually conjugated to CRM197 carrier protein, or a mixture consisting of capsular polysaccharides from Streptococcus pneumoniae serotypes 1, 4, 5, 6B, 7F, 9V, 14, 18C, 19F and 23F individually conjugated to a carrier protein, wherein the capsular polysaccharides from Streptococcus pneumoniae serotypes 1, 4, 5, 6B, 7F, 9V, 14, and 23F are individually conjugated to protein D, the capsular polysaccharide from Streptococcus pneumoniae serotype 18C is conjugated to tetanus toxoid and the capsular polysaccharide from Streptococcus pneumoniae serotype 19F is conjugated to diphtheria toxoid. Said compositions are useful for the prevention and/or treatment of diseases caused by Streptococcus pneumoniae.

  本发明涉及包含链球菌肺炎8型的糖类与载体蛋白的结合物的免疫原组合物，以及由链球菌肺炎1、3、4、5、6A、6B、7F、9V、14、18C、19A、19F和23F型的胶囊多糖组成的混合物，分别与CRM197载体蛋白共轭，或由链球菌肺炎1、4、5、6B、7F、9V、14、18C、19F和23F型的胶囊多糖组成的混合物，分别与载体蛋白共轭，其中链球菌肺炎1、4、5、6B、7F、9V、14和23F型的胶囊多糖分别与蛋白D共轭，链球菌肺炎18C型的胶囊多糖与破伤风类毒素结合，链球菌肺炎19F型的胶囊多糖与白喉类毒素结合。该组合物对预防和/或治疗由链球菌肺炎引起的疾病有用。
• Hydrogen-Bond-Mediated Aglycone Delivery (HAD): A Highly Stereoselective Synthesis of 1,2-<i>cis</i>α-<scp>D</scp>-Glucosides from Common Glycosyl Donors in the Presence of Bromine
  作者：Jagodige P. Yasomanee、Alexei V. Demchenko

  DOI：10.1002/chem.201406589

  日期：2015.4.20

  H‐bond mediated aglycone delivery (HAD) method recently introduced by our laboratory. At first it was noticed that high α‐stereoselectivity is only obtained with S‐ethyl glycosyl donors and only in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST), in high dilution, and low temperature. Combining the mechanistic studies of the HAD reaction and bromine‐promoted glycosylations

  本文描述的是我们实验室最近引入的由吡啶甲酰基保护基辅助的H键介导的糖苷配基递送（HAD）方法的扩展。最初，人们注意到只有在高稀释度和低温下，仅在S-乙基糖基供体和三氟甲磺酸二甲基（甲硫基）ulf存在下，才能获得高α-立体选择性。将HAD反应的机理研究与溴促进的糖基化结合起来，可以设计出一种非常有效的方法，该方法可以对几乎所有常见的离去基团（S-苯基，S-甲苯基，S / O-亚氨酸酯）进行高度立体选择性的α-糖基化。在常规浓度和环境温度下。
• [EN] VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE SEROTYPE 8<br/>[FR] VACCINS CONTRE STREPTOCOCCUS PNEUMONIAE SÉROTYPE 8
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2016046420A1

  公开（公告）日：2016-03-31

  The present invention relates to synthetic saccharides of general formula (I) that are related to Streptococcuspneumoniae serotype 8 capsular polysaccharide, conjugates thereof and the use of said saccharides and conjugates for raising a protective immune response in a human and/or animal host. Furthermore, the synthetic saccharide structures of general formula (I) are useful as marker in immunological assays for detection of antibodies against Streptococcuspneumoniae bacteria.

  本发明涉及一般式（I）的合成糖苷，与肺炎链球菌8型蒽聚糖有关，以及它们的结合物，以及利用所述糖苷和结合物在人类和/或动物宿主中引发保护性免疫反应。此外，一般式（I）的合成糖苷结构可用作免疫学检测中的标记，用于检测针对肺炎链球菌细菌的抗体。
• Halobenzoyl groups in glycosylation: effect on stereoselectivity and reactivity of glycosyl donors
  作者：S. Visansirikul、J. P. Yasomanee、A. V. Demchenko

  DOI：10.1007/s11172-015-0987-2

  日期：2015.5

  Described herein is the synthesis and evaluation of a series of glycosyl donors equipped with halobenzoyl substituents at O(4) and O(6) to study their properties in glycosylations. Among possible effects that may include carbonyl participation or H-bond mediated aglycone delivery, our results indicate that halobenzoyls act via a different mode.

  本文描述的是一系列在 O(4) 和 O(6) 处配备卤代苯甲酰基取代基的糖基供体的合成和评估，以研究它们在糖基化中的特性。在可能包括羰基参与或 H 键介导的苷元传递的可能影响中，我们的结果表明卤代苯甲酰基通过不同的模式起作用。
• Effect of Remote Picolinyl and Picoloyl Substituents on the Stereoselectivity of Chemical Glycosylation
  作者：Jagodige P. Yasomanee、Alexei V. Demchenko

  DOI：10.1021/ja307355n

  日期：2012.12.12

  O-Picolinyl and O-picoloyl groups at remote positions (C-3, C-4, and C-6) can mediate glycosylation reactions by providing high or even complete facial selectivity for the attack of the glycosyl acceptor. The set of data presented herein offers a strong evidence of the intermolecular H-bond tethering between the glycosyl donor and glycosyl acceptor counterparts while providing a practical new methodology for the synthesis of either 1,2-cis or 1,2-trans linkages. Challenging glycosidic linkages including alpha-gluco, beta-manno, and beta-rhamno have seen obtained with high or complete stereocontrol.