2-azido-3,4-di-O-acetyl-2-deoxy-β-L-fucopyranosyl trichloroacetimidate | 583041-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3,4-di-O-acetyl-2-deoxy-β-L-fucopyranosyl trichloroacetimidate
• 英文别名: (2S,3R,4S,5S,6R)-5-azido-2-methyl-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS: 583041-03-6
• 化学式: C₁₂H₁₅Cl₃N₄O₆
• 分子量: 417.633
• InChiKey: QLYBVIQMCILRJU-PHQGFKKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  143.67
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-azido-3,4-di-O-acetyl-2-deoxy-β-L-fucopyranosyl trichloroacetimidate 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 三乙基硅基三氟甲磺酸酯 、 乙二胺 作用下， 以 乙醇 、 二氯甲烷 、 正丁醇 为溶剂， 反应 92.5h， 生成 4-methoxyphenyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-α-L-fucopyranosyl-(1->3)-4,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the EnterohemorrhagicEscherichia coliType O26:H

  摘要：

  L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H.

  DOI：

  10.1081/car-120020480
• 作为产物：
  描述：

  2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 在 sodium azide 、 ammonium cerium(IV) nitrate 、 potassium carbonate 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 33.5h， 生成 2-azido-3,4-di-O-acetyl-2-deoxy-β-L-fucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the EnterohemorrhagicEscherichia coliType O26:H

  摘要：

  L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H.

  DOI：

  10.1081/car-120020480

文献信息

• Synthesis of trisaccharide and a tetrasaccharide repeating unit corresponding to the O-antigen of Shiga toxin producing Escherichia coli O177
  作者：Manas Jana、Anup Kumar Misra

  DOI：10.1016/j.tet.2015.04.042

  日期：2015.6

  A trisaccharide and a tetrasaccharide repeating unit corresponding to the cell wall O-antigen of verotoxin producing Escherichia coli O177 strain have been synthesized in excellent yield using sequential stereoselective glycosylation strategy. A common trichloroacetimidate intermediate has been used for the incorporation of two l-fucosamine moieties in the target molecules.

  使用顺序立体选择性糖基化策略，以优异的产率合成了对应于产生毒素的大肠杆菌O177菌株的细胞壁O-抗原的三糖和四糖重复单元。常用的三氯乙酰亚氨酸酯中间体已用于在靶分子中掺入两个1-岩藻糖胺部分。
• [EN] VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE SEROTYPE 4<br/>[FR] VACCINS CONTRE LE SÉROTYPE 4 DU STREPTOCOCCUS PNEUMONIAE
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2016091399A1

  公开（公告）日：2016-06-16

  The present invention relates to synthetic saccharides of general formula (I) that are related to Streptococcus pneumoniae serotype 4 capsular polysaccharide and conjugates thereof. Said conjugate and a pharmaceutical composition containing said conjugate are useful for prevention and/or treatment of diseases associated with Streptococcus pneumoniae, and more specifically of diseases associated with Streptococcus pneumoniae serotype 4. Furthermore, the synthetic saccharides of general formula (I) are useful as marker in immunological assays for detection of antibodies against Streptococcus pneumoniae bacteria.

  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。
• 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。