(2S,3R,4S,5S)-5-azido-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate | 1239880-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S)-5-azido-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• 英文别名: 3,4-di-O-acetyl-2-azido-2-deoxy-L-fucopyranosyl trichloroacetimidate；[(2S,3R,4S,5S)-4-acetyloxy-5-azido-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 1239880-55-7
• 化学式: C₁₂H₁₅Cl₃N₄O₆
• 分子量: 417.633
• InChiKey: QLYBVIQMCILRJU-RSMLHNCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-5-azido-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate 、 benzyl (5-(((2S,3R,4S,5S,6R)-5-(((2S,4aR,6R,7R,8R,8aR)-7-azido-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-6-((benzyloxy)methyl)-3,4-bis(naphthalen-2-ylmethoxy)tetrahydro-2H-pyran-2-yl)oxy)pentyl)(benzyl)carbamate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  [EN] VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE SEROTYPE 4
  [FR] VACCINS CONTRE LE SÉROTYPE 4 DU STREPTOCOCCUS PNEUMONIAE

  摘要：

  本发明涉及通式(I)的合成糖类，其与肺炎链球菌4型胶囊多糖相关，以及其共轭物。所述共轭物和含有所述共轭物的制药组合物对预防和/或治疗与肺炎链球菌相关的疾病，尤其是与肺炎链球菌4型相关的疾病有用。此外，通式(I)的合成糖类在免疫学检测中作为标记物，用于检测针对肺炎链球菌细菌的抗体。

  公开号：

  WO2016091399A1

文献信息

• Chemical Synthesis Elucidates the Immunological Importance of a Pyruvate Modification in the Capsular Polysaccharide of <i>Streptococcus pneumoniae</i> Serotype 4
  作者：Claney L. Pereira、Andreas Geissner、Chakkumkal Anish、Peter H. Seeberger

  DOI：10.1002/anie.201504847

  日期：2015.8.17

  Carbohydrate modifications are believed to strongly affect the immunogenicity of glycans. Capsular polysaccharides (CPS) from bacterial pathogens are frequently equipped with a pyruvate that can be placed across the 4,6‐, 3,4‐, or 2,3‐positions. A trans‐2,3‐linked pyruvate is present on the CPS of the Gram‐positive bacterium Streptococcus pneumoniae serotype 4 (ST4), a pathogen responsible for pneumococcal

  据信碳水化合物修饰强烈影响聚糖的免疫原性。来自细菌病原体的荚膜多糖（CPS）经常配备丙酮酸盐，可以放置在4,6、3、4或2,3位。革兰氏阳性细菌肺炎链球菌血清型4（ST4）的CPS上有一个反式的2,3连接的丙酮酸，这是引起肺炎球菌感染的病原体。为了评估这种修饰在CPS重复单元中的免疫学重要性，首先进行了聚糖的首次全合成。含有一系列合成抗原的聚糖微阵列证明了针对天然ST4 CPS产生的抗体如何在四糖重复单元的背景下特异性识别丙酮酸。
• Convergent synthesis of a common pentasaccharide-repeating unit corresponding to the O-specific polysaccharide of Escherichia coli O4:K3, O4:K6, and O4:K12
  作者：Rajib Panchadhayee、Anup Kumar Misra

  DOI：10.1016/j.tetasy.2010.04.056

  日期：2010.4

  A convergent chemical synthesis of a pentasaccharide found in the O-specific polysaccharide of Escherichia coli O4.K3, O4:K6, and O4:K12 has been achieved in excellent yield. A [3+2] block synthetic strategy has been adopted to couple a disaccharide donor 11 with a trisaccharide acceptor 10 for the construction of the pentasaccharide derivative 12 which on deprotection furnished target pentasaccharide 1 as its 4-methoxyphenyl glycoside Disaccharide thioglycoside donor 11 and trisaccharide acceptor 10 were prepared from suitably protected monosaccharide intermediates Yields were excellent in all steps. (C) 2010 Elsevier Ltd All rights reserved.